(2S)-1,1,1-Trifluoropropan-2-ol → HCID 86684905, compound

Participants

Reaction Conditions

Reaction Steps

(S)-1,1,1-Trifluoro-propan-2-ol (100 g, 877 mmol) was dissolved in dimethylacetamide (600 mL) and the solution was cooled to 2° C. (ice bath). A solution of sodium tert-butoxide (77.5 g, 790 mmol) in dimethylacetamide (100 mL) was added at 2° C. and the mixture was stirred for 15 min. This solution was treated with a solution of 2-chloro-4-fluoro-1-tritylsulfanyl-benzene (200 g, 494 mmol) in dimethylacetamide (100 mL) at room temperature and subsequently stirred for 3 h at 50° C. It was then poured into a mixture of brine (200 mL), ice (1.2 kg) and water (2.0 L), and extracted with tert-butyl-methylether (2×1000 mL). The combined organic extracts were washed with brine/water 1:1 (v/v, 300 mL) and concentrated in vacuo to give the crude product as a yellow viscous oil. The oil was dissolved in ethanol (1.6 L), before water (240 mL) was slowly added at room temperature. The resulting suspension was stirred for 14 h, cooled to 2° C. (ice bath) and stirred for another 2 h, before it was filtered. The solid was washed with ethanol/water 4:1 (v/v, 500 mL) and dried in vacuo to afford the title compound as a white crystalline solid (238 g, 97%). 1H NMR (CDCl3, 400 MHz): δ 1.43 (d, J=6.5 Hz, 3H), 4.50 (qq, J=6.2 Hz, 6.2 Hz, 1H), 6.44 (dd, J=2.8 Hz, 8.7 Hz, 1H), 6.84 (d, J=2.7 Hz, 1H), 6.90 (d, J=8.6 Hz, 1H), 7.18-7.27 (m, 9H), 7.33-7.39 (m, 6H).

Provenance & Evidence