Reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].C([Li])CCC.[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=1)([CH3:17])[CH3:16].O>C1COCC1>[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])([OH:28])[CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=1)([CH3:17])[CH3:16]Participants
Procedure
To a solution of 2-bromoanisole (5.0 g, 26.7 mmol) in THF (50 mL) was added n-butyllithium (1.6 M, 18 mL, 29 mmol) at −78° C., and the mixture was stirred at the same temperature for 30 minutes. To the reaction solution was added 1-(4-isopropylphenyl)-2-methylpropan-1-one (5.70 g, 30.0 mmol), and the mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture which was extracted with ethyl acetate, and the combined organic layer was washed with water, dried over magnesium sulfate, filtered and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 3.4 g (yield 43%) of the title compound. Melting point: 85-86° C. (methanol).
Workup
- stirringthe mixture was stirred at room temperature for 1 hour
- extractionwas extracted with ethyl acetate
- washthe combined organic layer was washed with water
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)
Sources & evidence
- ORD record
- ord-10463635bd034e0bb913030ee8f322a7
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07507841B2
Linked notes
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