Tetrahydrofuran → Methyl 6-(benzenesulphonylmethyl)-3-ethyl-2-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoate (Intermediate 65, 1.31 g) and potassium phosphate (2.02 g) in THF (9 ml) and water (4.5 ml) was degassed and palladium chloride dppf adduct with DCM (0.134 g) and triethyl borane (1M solution in THF, 4.6 ml) were added. The mixture was stirred and heated in the microwave at 140° C. for 18 minutes. The mixture was partitioned between ethyl acetate and water and the organic layer was separated, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 5-40% to give methyl 6-(benzenesulphonylmethyl)-3-ethyl-2-methoxybenzoate (0.754 g) as a colourless oil.

Provenance & Evidence