Chlorotrimethylsilane → 1-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-fluoro-phenyl]-ethanone
Reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:19])([CH3:18])[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][C:9]=1[F:17])([CH3:4])([CH3:3])[CH3:2].C[Li].[CH3:22][Si](C)(C)Cl>C1COCC1.C(OCC)C>[C:1]([SiH2:5][O:6][C:7]([CH3:19])([CH3:18])[C:8]1[CH:16]=[CH:15][C:11]([C:12](=[O:14])[CH3:22])=[CH:10][C:9]=1[F:17])([CH3:2])([CH3:3])[CH3:4]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -30 °C
Procedure
A solution of 540 mg (1.90 mmol) 4-(tert-butyl-dimethyl-silanyloxymethyl)-3-fluoro-benzoic acid (preparation 16d) in 20 mL THF is degassed and cooled to −30° C. 3.56 mL (5.67 mmol) 1.6 M methyl-lithium solution in diethylether is added, the mixture is stirred 2 h at −30° C. and 3.12 mL (24.7 mmol) trimethyl-chloro-silane are added. The mixture is stirred 2 min and is transferred to a pH 7 buffer solution (0° C.). The aqueous phase is extracted with EtOAc and diethylether. The combined organic phase is washed with water, dried over MgSO4, filtered and the solvent is evaporated. The residue is purified by silica gel column chromatography with PE/EtOAc (9:1) as eluent.
Workup
- stirringThe mixture is stirred 2 min
- extractionThe aqueous phase is extracted with EtOAc and diethylether
- washThe combined organic phase is washed with water
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe solvent is evaporated
- customThe residue is purified by silica gel column chromatography with PE/EtOAc (9:1) as eluent
Sources & evidence
- ORD record
- ord-3728810dc56841088d6144d8f6520bcf
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067590B2
Reaction notes
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