Diethyl Ether → 3-((Tert-butyldimethylsilyl)oxy)propanal

Participants

Reaction Steps

To a suspension of pyridinium chlorochromate (8.50 g, 39.4 mmol) in dichloromethane (53 ml), stirred at room temperature under dry nitrogen, was added 3-(t-butyldimethylsilyloxy)propan-1-ol (5.00 g, 26.3 mmol). After 1.5 hr, dry ether (50 ml) was added and the supernatant liquid decanted from a black gum. The residual gum was washed with ether (3×50 ml) and the combined organic portions passed through a column of Florisil. The resulting brown solution was evaporated then the residue taken up in dichloromethane and passed through fresh Florisil to give a yellow solution from which the solvent was removed to leave a brown liquid (2.75 g). This material was shown by 1Hnmr analysis to be approximately 40% pure and was used without further purification; δH (CDCl3) 0.10 (6H, s, CH3), 0.93 (9H, s, C(CH3)3), 0.63 (2H, dt, J 2 HZ and 6 Hz respectively, CH2), 4.03 (2H, t, J 6 Hz, CH2O ), 9.97 (1H, d, J 2 Hz, CHO).

Provenance & Evidence