Tetrabutylammonium Fluoride → 2-Fluoro-5-(4-fluorophenyl)-5-methylhex-1-en-3-ol
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH3:12])[CH2:9][CH:10]=[O:11])=[CH:4][CH:3]=1.[F:14][C:15](C[SiH](C1C=CC=CC=1)C1C=CC=CC=1)=[CH2:16].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:14][C:15]([CH:10]([OH:11])[CH2:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)([CH3:13])[CH3:12])=[CH2:16]Participants
Procedure
To a mixture of 3-(4-fluorophenyl)-3-methylbutyraldehyde (1.2 g, 6.6 mmol) and (1-fluorovinyl)methyldiphenylsilane in 5 mL of THF cooled on ice under nitrogen gas was added 1 mL of TBAF (1 M in THF). The mixture was allowed to warm to room temperature and left overnight. The solvent was evaporated and the residue was taken up in hexanes. The hexane soluble material was fractionated over silica gel (eluent: hexanes to hexanes-ethyl acetate (98:2)) to give a fraction (3.1 g) containing silylated product along with other silanes. This fraction was dissolved in 5 mL of THF and 10 mL of TBAF solution (1 M in THF) was added. The mixture was left at room temperature for 20 minutes, diluted with hexanes-ethyl acetate, and washed with water, dried, filtered, and concentrated in vacuo. Fractionation of the residue over silica gel (eluent: hexanes-ethyl acetate (99:1 to 9:1 gradient)) gave 1.73 g of the crude 2-fluoro-5-(4-fluorophenyl)-5-methylhex-1-en-3-ol as an oil which was used without additional purification.
Workup
- temperaturecooled on ice under nitrogen gas
- customThe solvent was evaporated
- customto give a fraction (3.1 g)
- waitThe mixture was left at room temperature for 20 minutes
- additiondiluted with hexanes-ethyl acetate
- washwashed with water
- customdried
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-604215ec77cf46f7be9dc5f5379afe03
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08741897B2
Reaction notes
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