Cesium fluoride → HCID 89719329, compound

Temperature

2.5 °C

Trimethyl(trifluoromethyl)silane (3.13 mL, 21.20 mmol) was added to a mixture of ethyl 2-(3-formylphenyl)acetate (2.91 g, 15.14 mmol) and cesium fluoride (0.161 g, 1.060 mmol) in DMF (20.19 mL) cooled to 0-5° C. After stirring for 1.5 hour, a solution of TBAF 1M in THF (15.14 mL) was added. The resulting yellow solution was stirred at 0-5° C. and after 30 minutes, the mixture was poured into water (150 mL) and extracted with MTBE (1×150 mL, then 2×100 mL). The combined organic layers were washed with water (1×150 mL then 1×100 mL) and with brine (100 mL) and then the organic layer was dried over anh. MgSO4, filtered and concentrated to give 3.84 g as a light orange oil which was purified by flash chromatography to give ethyl 2-(3-(2,2,2-trifluoro-1-hydroxyethyl)phenyl)acetate (663 mg, 16% yield) as a colorless oil: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.17 (t, J=7.0 Hz, 3H) 3.68 (s, 2H) 4.08 (q, J=7.0 Hz, 2H) 5.13 (q, J=7.4 Hz, 1H) 6.82 (s, 1H) 7.24-7.31 (m, 1H) 7.37 (t, J=7.2 Hz, 3H); MS m/z 263.1 (M+H)+; HPLC 93.7% @ 220 nm, RT=1.82 minutes.

1. stirringThe resulting yellow solution was stirred at 0-5° C. and after 30 minutes
2. extractionextracted with MTBE (1×150 mL
3. washThe combined organic layers were washed with water (1×150 mL
4. dry with material1×100 mL) and with brine (100 mL) and then the organic layer was dried over anh. MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto give 3.84 g as a light orange oil which
8. customwas purified by flash chromatography

ORD record

ord-9d9d4e4339a140b8840f9d237ec6634f

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296744B2