(Z)-3-(Tributylstannyl)prop-2-en-1-ol → Methyl 3-bromo-6-((2-(3-hydroxyprop-1-enyl)benzenesulfonyl)methyl)-2-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

Bis-(tri-tert-butylphosphine)palladium (0.031 g) was added to a degassed solution of methyl 3-bromo-6-(2-bromobenzenesulphonylmethyl)-2-methoxybenzoate (Intermediate 66, 0.286 g) and 3-tributylstannyl-(Z)-prop-2-en-1-ol (prepared according to Webb et al, Tetrahedron, 2008, 64, 4778, 0.27 ml) in toluene (3 ml) and the resultant mixture was stirred at room temperature for 3 hours then heated at 30° C. for 2 hours. After cooling, the mixture was filtered through Celite and 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 0-60% to give methyl 3-bromo-6-((2-(3-hydroxyprop-1-enyl)benzenesulfonyl)methyl)-2-methoxybenzoate as a mixture of E and Z isomers.

Provenance & Evidence