Chlorotrimethylsilane → HCID 18630022, compound
Reaction equation
[Li]C(CC)C.C1CCCCC1.CN(CCN(C)C)C.[F:20][C:21]1[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=1)[C:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25].[CH3:34][Si:35](Cl)([CH3:37])[CH3:36]>C1COCC1.CCOCC>[F:20][C:21]1[C:22]([Si:35]([CH3:37])([CH3:36])[CH3:34])=[C:23]([C:31]([Si:35]([CH3:37])([CH3:36])[CH3:34])=[CH:32][CH:33]=1)[C:24]([N:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1)=[O:25]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -90 °C
Procedure
A solution of 1.3M s-BuLi in cyclohexane (23.91 mL, 31.1 mmol) was added to an ether/liquid N2 cooled (-90° C.) solution of TMEDA (3.97 g, 34.2 mmol) in THF (40 mL), followed by the addition of a solution of N-(3-fluorobenzoyl)pyrrolidine (5.0 g, 25.9 mmol) in a minimum volume of THF. The resulting reaction mixture was stirred at -90° C. for 15 min, then TMSCl (6.75 g, 62.2 mmol) was added in a single portion. The reaction was warmed to RT, quenched with dilute aq citric acid, then was extracted with ether (3X). The combined ether extracts were dried (MgSO4), concentrated, and purified by HPLC with 3:7 EtOAc/hexanes to afford 0.45 g of the title compound as an oil, a 45% yield, which solidified on standing to a white solid. m.p. 97°-100° C.
Workup
- customThe resulting reaction mixture
- temperatureThe reaction was warmed to RT
- customquenched with dilute aq citric acid
- extractionwas extracted with ether (3X)
- dry with materialThe combined ether extracts were dried (MgSO4)
- concentrationconcentrated
- custompurified by HPLC with 3:7 EtOAc/hexanes
Sources & evidence
- ORD record
- ord-a221860d3a8c49a99d008d215e82d3a4
- Source dataset
- uspto-grants-1998_11
- Patent number
- US05834447
Reaction notes
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