Chlorotrimethylsilane → HCID 10710925, compound
Reaction equation
[Li]C(CC)C.C1CCCCC1.C(=O)=O.CC(C)=O.[CH2:19]([N:21]([CH:30]([O:35][CH3:36])[C:31]([CH3:34])([CH3:33])[CH3:32])[C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:20].CN(CCN(C)C)C.[CH3:45][Si:46](Cl)([CH3:48])[CH3:47]>C1COCC1>[CH2:19]([N:21]([CH:30]([O:35][CH3:36])[C:31]([CH3:32])([CH3:34])[CH3:33])[C:22](=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=1[Si:46]([CH3:48])([CH3:47])[CH3:45])[CH3:20]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of 1.3M s-BuLi in cyclohexane (140.6 mL, 182.8 mmol) was added dropwise to a dry-ice/acetone cooled solution of N-ethyl-N-(1-methoxy-2,2-dimethylpropyl)benzamide (35 g, 140.6 mmol) and TMEDA (25.44 mL, 168.6 mmol) in THF (280 mL), maintaining the internal reaction temperature ≤-60° C. The yellow solution was stirred at -78° C. for 1 h, then was cannulated into a dry-ice/acetone cooled solution of TMSCl (26.72 mL, 210.6 mmol) in THF (140 mL) at a rate which maintained the internal reaction temperature ≤-55° C. The resulting mixture was warmed to 0° C. and partitioned between ether and sat aq NaHCO3. The ether solution was dried (MgSO4), concentrated, and kugelrohr distilled under vacuum to give 44.8 g of the title compound as a pale yellow solid, a 99% yield. m.p. 76-78° C.
Workup
- temperaturemaintaining the internal reaction temperature ≤-60° C
- temperaturemaintained the internal reaction temperature ≤-55° C
- temperatureThe resulting mixture was warmed to 0° C.
- custompartitioned between ether
- dry with materialThe ether solution was dried (MgSO4)
- concentrationconcentrated
- distillationkugelrohr distilled under vacuum
Sources & evidence
- ORD record
- ord-d2a8519c82184349a50a3d1d46b1f5e2
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06028101
Reaction notes
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