Hydrochloric Acid → 5-(Trimethylsilyl)thiazole-2-carboxaldehyde

Participants

Reaction Steps

n-Butyllithium (1.50M in hexane, 39 mmol, 22 ml) was added dropwise at -78° C. to a solution of 5-(trimethylsilyl)thiazole (A. Dondoni et al, J. Org. Chem, 1988, 53, 1748) (5.2 g, 33 mmol) in THF (40 ml). After 30 min. a solution of N-formylmorpholine (4.57 g) in THF (40 ml) was added dropwise over 15 min. The resulting red solution was stirred a further 30 mi. and then allowed to warm to room temperature , dilute d with 4N hydrochloric acid and extracted three times with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride, dried over sodium sulphate and evaporated to leave a brown oil (5.5 g). M+ 185; 360 MHz 1H n.m.r (CDCl3) 9.89 (1H, s), 7.95 (1H, s), 0.24 (9H, s).

Provenance & Evidence