Sodium hydride → 2,2,2-Trifluoro-1-(4-fluorophenyl)ethyl trifluoromethanesulfonate

A dried 50 mL of flask was charged sodium hydride, 60% dispersion in mineral oil (624 mg, 15.6 mmol) under N2 and then washed with dried hexane (20 mL) twice. Dried ethyl ether (10 mL) was added and a solution of 2,2,2-trifluoro-1(RS)-(4-fluorophenyl)ethanol (90% ee) (2.5 g, 12.89 mmol) in ethyl ether (10 mL) was added at 0° C. After completion of addition, the reaction mixture was allowed to warm up to room temperature and stirred for 1 h. A solution of trifluoromethanesulfonyl chloride (3.28 g, 19.5 mmol) in ethyl ether (10 mL) was added at 0° C. After completion of addition, the reaction was allowed to warm up to room temperature and stirred for 1 h. The solvent was removed under rot-vap and diluted with hexane (150 mL) and washed with a saturated NaHCO3 n and brine. After drying with MgSO4, the organic solvent was removed to give trifluor-methanesulfonic acid 2,2,2-trifluoro-1(RS)-(4-fluorophenyl)ethyl ester (3.15 g) (90% ee) as a colorless oil which was used in the next step without further purification.

1. washwashed with dried hexane (20 mL) twice
2. additionDried ethyl ether (10 mL) was added
3. additionAfter completion of addition
4. additionAfter completion of addition
5. temperatureto warm up to room temperature
6. stirringstirred for 1 h
7. customThe solvent was removed under rot-vap
8. additiondiluted with hexane (150 mL)
9. washwashed with a saturated NaHCO3 n and brine
10. dry with materialAfter drying with MgSO4
11. customthe organic solvent was removed

ORDレコード

ord-8f39b88f41da4254a6a7667099ca1295

出典データセット

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07737300B2