Sodium Cyanide → 5-Iodo-2-thiophenecarboxaldehyde

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Reaction Steps

To a stirred solution of 3-t-butyl-3-formyl-oxetane (1.0 g) and 4-iodobenzoyl chloride (2.6 g) in dry diethyl ether (35 ml), under nitrogen, was added a solution of sodium cyanide (1.25 g) in water (1.0 ml). The mixture was stirred overnight. The mixture was poured into water (50 ml.) and the aqueous mixture was extracted with diethyl ether. The ethereal solution was dried over anhydrous sodium sulphate and then evaporated in vacuo. The residue was chromatographed on silica pre-treated with triethylamine eluting with hexane:chloroform 1:3. The 4-iodobenzoate of 3-t-butyl-3-(cyano-hydroxymethyl)-oxetane was obtained as a colourless solid (2.54 g.). Nuclear magnetic resonance spectrum (NMR) was as follows: 1H (ppm from TMS in CDCl3, integral, number of peaks): 7.90-7.70, 4H, q; 5.80, 1H, s; 4.80-4.60, 4H, m; 1.10, 9H, s.

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