(1R)-3-chloro-1-phenylpropan-1-ol → 7-[(1S)-3-Chloro-1-phenylpropyl]oxy-1-benzothiophene

Participants

Reaction Steps

4,4-(Dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-triphenyl phosphonium (327 mg, 0.80 mmol) was added in one portion to a stirred solution of (R)-(+)-3-chloro-1-phenyl-1-propanol (90 mg, 0.53 mmol) and 1-benzothiophen-7-ol (80 mg, 0.53 mmol) in dry THF (5 mL) under an inert atmosphere on nitrogen. The resulting suspension was allowed to stir for a further 18 hrs before the solvent was removed in vacuo. The residue was triturated with hexane (ca. 15 mL) and the solid filtered, the filtrate was concentrated in vacuo and the resulting pale yellow oil was purified by flash chromatography eluting silica gel with hexane:ether [95:5] to yield the title compound as a colourless oil (60 mg, 37%); Rf=0.8 in hexane:ether [10:1]; δH (300 MHz, CDCl3) 7.66–7.00 (9H, m, Ar); 6.55 (1H, d, Ar), 5.80–5.72 (1H, m, CHO), 3.91–3.60 (2H, m, CH2), 2.62–2.50 (1H, m, CHH), 2.38–2.22 (1H, m, CHH).

Provenance & Evidence