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

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.

1. stirringthe mixture was stirred at room temperature for 3 days
2. temperaturethe mixture was warmed at 60° C. for 2 hours
3. washwashed with water
4. customdried
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-9cdcad5474b1446cbfeac0a9d9ddc0cf

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741897B2