Sodium hydride → trifluoromethanesulfonic acid 2,2,2-trifluoro-1(R)-(4-fluorophenyl)ethyl ester

HRID 642901

Reaction equation

[H-].[Na+].[F:3][C:4]([F:15])([F:14])[C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[OH:6].[F:16][C:17]([F:23])([F:22])[S:18](Cl)(=[O:20])=[O:19]>CCOCC>[F:15][C:4]([F:3])([F:14])[C@H:5]([O:6][S:18]([C:17]([F:23])([F:22])[F:16])(=[O:20])=[O:19])[C:7]1[CH:8]=[CH:9][C:10]([F:13])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

NaH (11.87 g, 296.7 mmol) was added to Et2O (700 mL) at 0° C. under N2 followed by addition of an Et2O solution of 2,2,2-trifluoro-1(R)-(4-fluorophenyl)ethanol (44.3 g, 228.2 mmol). The reaction mixture was stirred for 10 min at 0° C. then 1 h at room temperature. Trifluoromethanesulfonyl chloride (50 g, 296.7 mmol) in Et2O was added at 0° C. under N2 and the reaction mixture was stirred 10 min at 0° C. then 3 h at room temperature. The solvent was removed under the reduced pressure and H2O (100 mL) was added slowly. The aqueous layer was extracted by hexane and the combined organic layer was dried over MgSO4. The solvent was removed under the reduced pressure to give trifluoromethanesulfonic acid 2,2,2-trifluoro-1(R)-(4-fluorophenyl)ethyl ester (70 g) as colorless oil.

Workup

custom1 h
customat room temperature
stirringthe reaction mixture was stirred 10 min at 0° C.
custom3 h
customat room temperature
customThe solvent was removed under the reduced pressure and H2O (100 mL)
additionwas added slowly
extractionThe aqueous layer was extracted by hexane
dry with materialthe combined organic layer was dried over MgSO4
customThe solvent was removed under the reduced pressure

Sources & evidence

ORD record: ord-79da370cd4a74eccabbb5253c57ce4a7
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696250B2

Linked notes

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