Acetyl chloride → 1-(4'-t-Butyldimethylsilyloxy-3'-methoxyphenyl)-1-hexene-3,5-dione
Reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17](=[O:19])[CH3:18])=[CH:11][C:10]=1[O:20][CH3:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].[C:30](Cl)(=[O:32])[CH3:31].C(OCC)C.CCCCCC>C1COCC1>[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17](=[O:19])[CH2:18][C:30](=[O:32])[CH3:31])=[CH:11][C:10]=1[O:20][CH3:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of 1-(4'-t-butyldimethylsilyloxy-3'-methoxyphenyl)-1-butene-3-one (12.8 g, 41.8 mmol) in THF (50 mL) is cooled to -78° C. under an argon atmosphere. Lithium di-isopropyl amide (83.5 mmol, in 50 mL THF) is slowly added to the reaction mixture. The reaction is stirred at -78° C. for 30 minutes. Acetyl chloride (16.4 g, 209 mmol) dissolved in THF (20 mL) is then added to the reaction over a 30 minute period. The reaction is quenched with aqueous HCl. The layers are separated, and the aqueous layer is washed with ethyl acetate. The combined organic layers are washed with saturated aqueous sodium bicarbonate, dried over MgSO4, and evaporated to give a red oil. Flash chromatography (ethyl ether/hexane 2:8) afford 5.0 g (34%) of 1-(4'-t-butyldimethylsilyloxy-3'-methoxyphenyl)-1-hexene-3,5-dione, mp=81°-85° C.
Workup
- additionis then added to the reaction over a 30 minute period
- customThe reaction is quenched with aqueous HCl
- customThe layers are separated
- washthe aqueous layer is washed with ethyl acetate
- washThe combined organic layers are washed with saturated aqueous sodium bicarbonate
- dry with materialdried over MgSO4
- customevaporated
- customto give a red oil
Sources & evidence
- ORD record
- ord-186aaaab50cf4f78a911fcbf11917b72
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05208251
Reaction notes
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