Butyl vinyl ether → HCID 67107899, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 61, 0.82 g), triethylamine (0.7 ml), 1,3-bis(diphenylphosphino)propane (0.04 g) and palladium chloride (0.01 g) in ethylene glycol (4 ml) was sealed in a vial under nitrogen and the mixture was stirred and heated to 140° C. Butyl vinyl ether (0.8 ml) was then added and the resultant mixture was stirred and heated at 140° C. for 2 hours. After cooling, the mixture was diluted with DCM and 1M hydrochloric acid was added. The mixture was stirred at room temperature for 30 minutes then the two layers were separated and the aqueous layer was extracted with further DCM. The combined organic layers were dried (MgSO4) and filtered. The filtrate was evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-80%) to give crude ethyl 3-acetyl-6-(benzenesulphonylmethyl)-2-methoxybenzoate (0.33 g) as an oil.

Provenance & Evidence