Sodium Sulfite → 2-(t-Butoxycarbonylamino)-3-(t-butyldiphenylsiloxy)propanal

Participants

Reaction Steps

To a solution of 2-(t-butoxycarbonylamino)-3-(t-butyldiphenylsiloxy)propanol (3.03 g) in methylene chloride (100 ml), Dess-Martin periodinane (3.60 g) was added at room temperature. The resulting mixture was stirred for 30 minutes. To the reaction mixture, a saturated aqueous solution (50 ml) of sodium bicarbonate and a 10% aqueous solution (50 ml) of sodium sulfite were added to cause separation. The water layer was extracted with diethyl ether (50 ml). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by chromatography on a silica gel column (150 g of silica gel, hexane:ethyl acetate=4:1→3:1), whereby the title compound (2.97 g) was obtained as a colorless transparent oil.

Provenance & Evidence