Citric Acid → 2-[(1,1-Dimethylethyl)dimethylsilyl)-N,N-diethyl-3-fluoro-6-methylbenzamide
Reaction equation
[Li][CH:2](CC)C.C1CCCCC1.CN(CCN(C)C)C.[CH3:20][C:21]([Si:24]([CH3:40])([CH3:39])[C:25]1[C:37]([F:38])=[CH:36][CH:35]=[CH:34][C:26]=1[C:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[O:28])([CH3:23])[CH3:22].CI.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:20][C:21]([Si:24]([CH3:40])([CH3:39])[C:25]1[C:37]([F:38])=[CH:36][CH:35]=[C:34]([CH3:2])[C:26]=1[C:27]([N:29]([CH2:30][CH3:31])[CH2:32][CH3:33])=[O:28])([CH3:23])[CH3:22]Participants
8
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
1.3M s-BuLi in cyclohexane (1.8 mL, 2.3 mmol) was added dropwise with stirring to THF (20 mL) and TMEDA (0.32 g, 2.76 mmol), cooled to -78° C. under nitrogen. To this mixture was added dropwise the compound of Example 9 (0.6 g, 2 mmol), dissolved in a minimum amount of THF. After stirring for 10 min, MeI (0.98 g, 6.9 mmol) was injected. The mixture was stirred for 1 h; 15 mL of 25% citric acid was added and the mixture extracted with ether 3 times. The ether extracts were combined and washed twice with water, dried (MgSO4), and concentrated. The crude product was purified by RC, eluting with 3:7 ethyl acetate/hexanes. The title compound was obtained as a light yellow oil in a 31% yield.
Workup
- stirringThe mixture was stirred for 1 h
- extractionthe mixture extracted with ether 3 times
- washwashed twice with water
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe crude product was purified by RC
- washeluting with 3:7 ethyl acetate/hexanes
Sources & evidence
- ORD record
- ord-41c0a16688aa476faf10d3af3682ba81
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05811411
Reaction notes
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