Water → 3-Thiopheneethanol methanesulfonate

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Reaction Steps

Methylsulfonyl chloride (2.22 ml, 28.75 mmol) was added dropwise to a solution of 3-thiopheneethanol (2.46 g, 19.2 mmol) and Et3N (5.3 ml) in DCM (50 ml) as 0° C. The mixture was stirred for 15 min before DCM and water was added. Organic phase was separated and residue purified by flash chromatography using 20-25% EtOAc in iso-hexane as eluents. Yield: 3.93 g (99%); colourless oil. HPLC: RT=2.20 min, 96% (254 nm, 10-90% MeCN in 0.1% TFA, 3 min ACE). 1H NMR (400 MHz, CDCl3): δ 2.90 (s, 3H), 3.13 (t, J 6.8 Hz, 2H), 4.44 (t, J 6.8 Hz, 2H), 7.00-7.02 (m, 1H), 7.11-7.12 (m, 1H), 7.32-7.36 m, 1H).

Provenance & Evidence