Hydrochloric Acid → 4-[1-Hydroxy-4,5-di(t-butyldimethylsilyloxy)-3-oxohexyl]oxazole

Participants

Reaction Conditions

Reaction Steps

A solution of 3,4-di)t-butyldimethylsilyloxy)pentan-2-one (4, 2.8 g, 8 mmol,) in THF (10 mL) was added to -70° C. solution of litium diisopropylaminde (LDA, 8 mmol) in THF (20 mL). After 10 minutes at -70° C., a solution of 4-formyloxazole (1.0 g, 8 mmol--Preparation 15) in THF (5 mL) was added and the resulting mixture allowed to warm to 0° C. Aqueous HCl was added and the mixture extracted with ether. The organic layer was washed with water and brine, dried over MgSO4, evaporated and the residue purified by medium pressure chromatography (0-50% hexane-ethyl acetate gradient) to yield 4-[1-hydroxy-4,5-di-(t-butyldimethylsilyloxy)-3-oxohexyl]oxazole (5).

Provenance & Evidence