Methanol → methyl (2R)-2-hydroxy-4-iodobutanoate

Participants

Reaction Steps

To a solution of (3R)-3-hydroxydihydro-2(3H)-furanone (1.6 g, 16 mmol) and methanol (0.65 g, 16 mmol) in dichloromethane (50 mL) under N2 at −10° C. was added TMSI (3.4 g, 17 mmol) over 0.5 hour. The mixture was stirred at the same temperature for 1 hour and was then allowed to warm up to room temperature and stirred for another 3 hours. TLC (PE:EA=1:1) showed that the reaction was completed. The mixture was washed with saturated aqueous NaHCO3 (20 mL), 2% aq. Na2S2O3 (20 mL) and brine (20 mL), dried (Na2SO4), and concentrated in vacuo to provide methyl (2R)-2-hydroxy-4-iodobutanoate as a yellowish oil (3.35 g, 85%). 1H NMR (300 MHz, CDCl3) δ 4.26-4.23 (m, 1H), 3.79 (s, 3H), 3.29-3.26 (t, 2H), 2.83 (s, 1H), 2.38-2.25 (m, 1H), 2.19-2.01 (m, 1H).

Provenance & Evidence