Ethyl trimethylsilylacetate → Ethyl 3-(4-fluorophenyl)-3-(4-hydroxyphenyl)-acrylate
Reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C[Si]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])(C)C.[F:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)=O)=[CH:24][CH:23]=1>C1COCC1>[F:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)=[CH:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:26][CH:27]=1Participants
Procedure
A solution of lithium hexamethyldisilazide (23.1 mL, 1 M in THF) was added to a stirred solution of ethyl (trimethylsilyl)acetate (2.53 mL, 13.9 mmol) in THF (15 mL) in 10 minutes at −78° C. The reaction mixture was further stirred at this temperature for 20 minutes. A solution of (4-fluoro-phenyl)-(4-hydroxy-phenyl)-methanone (2 g, 9.2 mmol) in THF (30 mL) was slowly added to the reaction mixture. The reaction mixture was brought to 0° C. over 5 hours. The reaction mixture was quenched with saturated NH4Cl solution, extracted into EtOAc and washed with dilute NH4Cl solution. The organic layer was dried over magnesium sulfate. The solvent was removed under vacuum, and the resulting product was flash chromatographed on silica gel, giving M2.1 as an oil.
Workup
- waitThe reaction mixture was brought to 0° C. over 5 hours
- customThe reaction mixture was quenched with saturated NH4Cl solution
- extractionextracted into EtOAc
- washwashed with dilute NH4Cl solution
- dry with materialThe organic layer was dried over magnesium sulfate
- customThe solvent was removed under vacuum
- customchromatographed on silica gel
- customgiving M2.1 as an oil
Sources & evidence
- ORD record
- ord-fec2b927e8784b2f888ca667156507b1
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687526B2
Reaction notes
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