(Z)-3-(Tributylstannyl)prop-2-en-1-ol → (Z)-methyl 3-bromo-6-((4-fluoro-2-(3-hydroxyprop-1-enyl)benzenesulfonyl)methyl)-2-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-bromo-6-(2-bromo-4-fluorobenzenesulphonylmethyl)-2-methoxybenzoate (Intermediate 163, 0.916 g), 3-tributylstannyl-(Z)-prop-2-en-1-ol (prepared according to Webb et al, Tetrahedron, 2008, 64, 4778, 0.833 g) and tris(dibenzylideneacetone)dipalladium (0) (0.085 g) in toluene (12 ml) was degassed with argon. Tri-tert-butylphosphine (1M in toluene, 0.20 ml) was added and the mixture was again degassed then heated to 30° C. for 3 hours. After cooling, the mixture was diluted with ethyl acetate and filtered through a PTFE cone. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and pentane containing 1% triethylamine with a gradient of 0-100%, to give (Z)-methyl 3-bromo-6-((4-fluoro-2-(3-hydroxyprop-1-enyl)benzenesulfonyl)methyl)-2-methoxybenzoate (0.198 g) as a yellow oil.

Provenance & Evidence