Cesium fluoride → 2-Fluoro-5-(5-fluoro-2-methoxyphenyl)-5-methylhex-1-en-3-ol

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Reaction Steps

To a solution of 3-(5-fluoro-2-methoxyphenyl)-3-methylbutyraldehyde (1.1 g, 5.2 mmol) and the above (1-fluorovinyl)dimethylphenylsilane (2.2 g, 12.2 mmol) in 5 mL of THF was added 0.6 mL of tetrabutylammonium fluoride (1 M in THF) and the mixture was stirred at room temperature overnight. TLC showed partial conversion to product. Cesium fluoride (0.22 g) was added and the mixture was stirred at room temperature for 3 days. 2 mL of water and 2 mL of acetic acid were added and the mixture was warmed at 60° C. for 2 hours to effect desilylation of any silylated product. The mixture was diluted with ethyl acetate, washed with water, dried, filtered and concentrated in vacuo. Fractionation of the residue over silica gel (eluent: hexanes-dichloromethane (3:1 to 1:3 gradient) gave 0.798 g (59.5% yield) of 2-fluoro-5-(5-fluoro-2-methoxyphenyl)-5-methylhex-1-en-3-ol as an oil which was used without additional purification.

Provenance & Evidence