Hydrochloric Acid → HCID 14281435, compound

Participants

Reaction Conditions

Reaction Steps

Butyllithium (n-Buli, 0.32 g, 5 mmol) in hexane is added to a -50° C. Solution of 4-[1,3,4,5-tetra(t-butyldimethylsilyloxy)hexyl]oxazole (6, 3.4 g, 5 mmol) in THF (50 mL). The resulting solution stirred at -50° C. for three hours. A solution of 5-formyloxazole (0.53 g, 5.5 mmol - Preparation 20) in THF (7 mL) is added, and the mixture allowed to warm to room temperature while stirring for 12 hours. The resulting mixture is added to water, acidified with HCl and extracted three times with ether. The organic layer is washed with aqueous Na2SO3 and brine, dried over Na2SO4, and evaporated to yield 2-[1-(oxazol-5-yl)-1-hydroxymethyl]-4-[1,3,4,5-tetra(t-butyldimethylsilyloxy)hexyl]oxazole (7).

Provenance & Evidence