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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 354056656
| Watchedfields = changed
⚫ | ImageFile = Pirkle's alcohol.png
⚫ | verifiedrevid = 446534618
⚫ | ImageFile = Pirkle alcohol.svg
| ImageSize = 200px | ImageSize = 200px
| IUPACName = 1-Anthracen-9-yl-2,2,2-trifluoroethanol | IUPACName = 1-Anthracen-9-yl-2,2,2-trifluoroethanol
| OtherNames = 2,2,2-Trifluoro-1-(9-anthryl)ethanol | OtherNames = 2,2,2-Trifluoro-1-(9-anthryl)ethanol
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = 65487-67-4 | CASNo = 65487-67-4
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
⚫ | CASNo1 = 53531-34-3
| UNII = 5K227FG858
⚫ | CASNo1_Ref = {{cascite|correct|CAS}}
⚫ | CASNo1 = 53531-34-3
⚫ | CASNo1_Comment = (''R'')
⚫ | CASNo1_Ref = {{cascite|correct|CAS}}
⚫ | CASNo2 = 60646-30-2
⚫ | CASNo1_Comment = (''R'')
⚫ | CASNo2_Ref = {{cascite|correct|CAS}}
⚫ | CASNo2 = 60646-30-2
⚫ | CASNo2_Comment = (''S'')
| CASNo2_Ref = {{cascite|correct|CAS}}
⚫ | PubChem =
⚫ | CASNo2_Comment = (''S'')
⚫ | SMILES = OC(C(F)(F)F)C1=C2C(C=CC=C2)=CC3=CC=CC=C31
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 93716
| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1 = 5370700
| ChemSpiderID1_Comment = (''R'')
| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID2 = 2006270
| ChemSpiderID2_Comment = (''S'')
⚫ | PubChem = 103802
| PubChem1 = 7006444
| PubChem1_Comment = (''R'')
| PubChem2 = 2724111
| PubChem2_Comment = (''S'')
⚫ | SMILES = OC(C(F)(F)F)C1=C2C(C=CC=C2)=CC3=CC=CC=C31
| SMILES1 = FC(F)(F)(O)c2c3c(cc1c2cccc1)cccc3
| SMILES1_Comment = (''R'')
| SMILES2 = C1=CC=C2C(=C1)C=C3C=CC=CC3=C2(C(F)(F)F)O
| SMILES2_Comment = (''S'')
| InChI = 1S/C16H11F3O/c17-16(18,19)15(20)14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9,15,20H
| InChIKey = ICZHJFWIOPYQCA-UHFFFAOYSA-N
| InChI1 = 1S/C16H11F3O/c17-16(18,19)15(20)14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9,15,20H/t15-/m1/s1
| InChIKey1 = ICZHJFWIOPYQCA-OAHLLOKOSA-N
| InChI1_Comment = (''R'')
| InChI2 = 1S/C16H11F3O/c17-16(18,19)15(20)14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9,15,20H/t15-/m0/s1
| InChIKey2 = ICZHJFWIOPYQCA-HNNXBMFYSA-N
| InChI2_Comment = (''S'')
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=16|H=11|F=3|O=1 | C=16 | H=11 | F=3 | O=1
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}


'''Pirkle's alcohol''' is an off-white, crystalline solid that is stable at room temperature when protected from light and oxygen. This ] molecule is typically used, in nonracemic form, as a ] in ], in order to simultaneously determine ] and ] purity of other chiral molecules. The molecule is named after William H. Pirkle, Professor of Chemistry at the University of Illinois whose group reported its synthesis and its application as a chiral shift reagent.<ref>{{cite journal | title = Nuclear magnetic resonance determination of enantiomeric composition and absolute configuration of &gamma;-lactones using chiral 2,2,2-trifluoro-1-(9-anthryl)ethanol | author = William H. Pirkle, David L. Sikkenga, Mark S. Pavlin | journal = ] | year = 1977 | volume = 42 | issue = 2 | pages = 384–387 | doi = 10.1021/jo00422a061}}</ref> '''Pirkle's alcohol''' is an off-white, crystalline solid that is stable at room temperature when protected from light and oxygen. This ] molecule is typically used, in nonracemic form, as a ] in ], in order to simultaneously determine ] and ] purity of other chiral molecules. The molecule is named after William H. Pirkle, Professor of Chemistry at the University of Illinois whose group reported its synthesis and its application as a chiral shift reagent.<ref>{{cite journal | title = Nuclear magnetic resonance determination of enantiomeric composition and absolute configuration of γ-lactones using chiral 2,2,2-trifluoro-1-(9-anthryl)ethanol |author1=William H. Pirkle |author2=David L. Sikkenga |author3=Mark S. Pavlin | journal = ] | year = 1977 | volume = 42 | issue = 2 | pages = 384–387 | doi = 10.1021/jo00422a061}}</ref>


==Synthesis== ==Synthesis==
Pirkle’s alcohol is synthesized by trifluoroacetylation of ], to yield trifluoromethyl 9-anthryl ]. Trifluoromethyl 9-anthryl ketone may be reduced with a chiral hydride reagent prepared from ] and (4S,5S)-(–)-2-ethyl-4-hydroxymethyl-5-phenyl-2-oxazoline to generate Pirkle’s alcohol with R absolute configuration. Alternatively, trifluoromethyl 9-anthryl ketone may be reduced with ] to generate racemic Pirkle’s alcohol. The enantiomers are then derivatized to ] ]s using enantioenriched 1-(1-Naphthyl)ethyl ] (also developed by Pirkle). These diastereomers may be separated by ] and ] to obtain each enantiomer of Pirkle’s alcohol in enantiopure form. Pirkle's alcohol is synthesized by trifluoroacetylation of ], to yield trifluoromethyl 9-anthryl ]. Trifluoromethyl 9-anthryl ketone may be reduced with a chiral hydride reagent prepared from ] and (4S,5S)-(–)-2-ethyl-4-hydroxymethyl-5-phenyl-2-oxazoline to generate Pirkle's alcohol with R absolute configuration. Alternatively, trifluoromethyl 9-anthryl ketone may be reduced with ] to generate racemic Pirkle's alcohol. The enantiomers are then derivatized to ] ]s using enantioenriched 1-(1-Naphthyl)ethyl ] (also developed by Pirkle). These diastereomers may be separated by ] and ] to obtain each enantiomer of Pirkle's alcohol in enantiopure form.


==Application== ==Application==
The determination of enantiomeric purity and absolute configuration is frequently necessary in ]. Pirkle’s alcohol is applied to obtain this information by ]. When Pirkle’s alcohol is in solution with an ensemble of chiral molecules, short-lived diastereomeric solvates may be formed from Pirkle’s alcohol and the enantiomers of the analyte. ] protons of the analyte enantiomers, which without Pirkle’s alcohol are indistinguishable by NMR, become diastereomorphic when the analyte interacts with Pirkle’s alcohol, and appear as different signals in an NMR spectrum. The relative magnitude of the signals quantitatively reveals the enantiomeric purity of the analyte. Also, a model of the solvated complex may be used to deduce absolute configuration of an enantioenriched analyte. The determination of enantiomeric purity and absolute configuration is frequently necessary in ]. Pirkle's alcohol is applied to obtain this information by ]. When Pirkle's alcohol is in solution with an ensemble of chiral molecules, short-lived diastereomeric solvates may be formed from Pirkle's alcohol and the enantiomers of the analyte. ] protons of the analyte enantiomers, which without Pirkle's alcohol are indistinguishable by NMR, become diastereomorphic when the analyte interacts with Pirkle's alcohol, and appear as different signals in an NMR spectrum. The relative magnitude of the signals quantitatively reveals the enantiomeric purity of the analyte. Also, a model of the solvated complex may be used to deduce absolute configuration of an enantioenriched analyte.

==See also==
* ]
* ]


==References== ==References==
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