Ethyl bromoacetate → HCID 20031089, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of sodium hyride (0.63 g) in THF (65 ml) was treated with the compound of Example 77 (4.0 g) and heated at 60° C. for 3 hours. Ethyl bromoacetate (10.9 g) was added to the cooled mixture and the reaction was allowed to proceed at ambient temperature overnight. The crude methoxy acetic acid ethyl ester was poured into ethanol (200 ml), treated with 3N sodium hydroxide and heated at reflux temperature for 1.5 hours. The solution was concentrated to 100 ml, diluted to 250 ml with water and unreacted compound of Example 77 extracted into ethyl acetate. The aqueous phase was acidified and crude product filtered. Ethanol crystallization gave the title compound (2.18 g, m.p. 123° C.). An analytical sample, m.p. 183° C., was obtained from ethanol solution.

Provenance & Evidence