Citric Acid → HCID 54249709, compound
Reaction equation
[Li][CH:2]([CH2:4][CH3:5])[CH3:3].[CH2:6]1[CH2:11]CCCC1.[C:12](=[O:14])=O.CC(C)=O.C[N:20]([CH2:22][CH2:23]N(C)C)C.C(NC(=O)C1C=CC=CC=1[Cl:37])C.[C:39]1([Si:45]([CH3:49])([CH:47]=[CH2:48])Cl)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[Cl:37][C:3]1[CH:6]=[CH:11][CH:5]=[C:4]([Si:45]([CH:47]=[CH2:48])([CH3:49])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:2]=1[C:12]([NH:20][CH2:22][CH3:23])=[O:14]Participants
9
Reactant 7
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A 1.3M solution of s-BuLi in cyclohexane (10.5 mL, 13.6 mmol) was added to a dry ice/acetone cooled solution of TMEDA (1 mL, 6.5 mmol) in THF (10 mL), followed by the dropwise addition of the compound of example f (1.0 g, 5.45 mmol) in THF (10 mL). Phenyl methyl vinyl chlorosilane (1.5 g, 8.2 mmol) was added after 30 min, and the mixture was stirred at -78° C. for 2 h. This was poured into 25% aq citric acid and partitioned between EtOAc and water. The EtOAc was dried (MgSO4), concentrated, and purified by HPLC with 1:19 EtoAc/cyclohexane to afford 0.56 g of a white solid which was recrystallized from EtOAc/petroleum ether at low temperature to give 0.194 g of title compound, an 11% yield. m.p. 85-87° C.
Workup
- custompartitioned between EtOAc and water
- dry with materialThe EtOAc was dried (MgSO4)
- concentrationconcentrated
- custompurified by HPLC with 1:19 EtoAc/cyclohexane
Sources & evidence
- ORD record
- ord-80684eac622647e78ad4981fb31769e7
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998466
Reaction notes
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