Phosphate → (S)-alpha-(Trifluoromethyl)benzyl alcohol

HRID 346435

Reaction equation

P([O-])([O-])([O-])=O.[F:6][C:7]([F:17])([F:16])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].CC(O)C>C(OCC)(=O)C>[F:6][C:7]([F:16])([F:17])[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9]

Participants

Conditions

Temperature: 30 °C

Procedure

To 0.02 g of the aforementioned wet bodies was added 500 μl of 50 mM phosphate buffer (pH 7.0) containing 1% 2,2,2-trifluoroacetophenone and 5% 2-propanol, followed by stirring at 30° C. for 18 hours. Then, after adding 500 μl of ethyl acetate to the reaction mixture, the mixture was subjected to centrifugal separation to obtain the organic phase. The organic phase was subjected to an analysis of the content by way of gas chromatography under the following condition. 2,2,2-Trifluoro-1-phenylethanol was produced at a ratio of 49.4% based on the amount of 2,2,2-trifluoroacetophenone used in the reaction. Furthermore, optical purity of 2,2,2-trifluoro-1-phenylethanol in the organic phase was measured under the following condition. The (S)-form of 99% e.e. was demonstrated.

Workup

customthe mixture was subjected to centrifugal separation
customto obtain the organic phase

Sources & evidence

ORD record: ord-3b169d156aa444c09b848c7a39e4a6d4
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07172894B2

Linked notes

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