Hydrochloric Acid → (R)-3-mesyloxy-2-hydroxy-1-chloropropane

Participants

Reaction Steps

Concentrated HCl (20 ml) was added to (S)-3-mesyloxy-1,2-epoxypropane (5.0 g, 0.033 m) over 15-20 minutes. After stirring for an additional 30 minutes, the water was removed through the addition and subsequent evaporation of ethanol. Finally, residual ethanol was removed at room temperature and 0.1 mm to give (R)-3-mesyloxy-2-hydroxy-1-chloropropane, (5.4 g, 85%); 1H NMR (CDCl3) 4.35 (2H, d), 4.1 (1H, m), 3.65 (2H, d), 3.1 (3H, s), 2.9 (1H, broad s); [α]D22 =7.1° (c=5.78, CH3OH).

Provenance & Evidence