Dimethylformamide → HCID 131731643, compound

HRID 1614839Notes

Reaction equation

HRID 1614839 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]23[CH2:16][CH:12]([C:13]2([CH3:15])[CH3:14])[CH2:11][CH2:10][CH:9]3[CH3:17])=[CH:4][C:3]=1[SiH:18]([CH3:20])[CH3:19].C([Li])CCC.CN(C)[CH:28]=[O:29]>C(OCC)C>[C:8]12([C:5]3[CH:6]=[CH:7][C:2]([CH:28]=[O:29])=[C:3]([SiH:18]([CH3:20])[CH3:19])[CH:4]=3)[CH2:16][CH:12]([C:13]1([CH3:15])[CH3:14])[CH2:11][CH2:10][CH:9]2[CH3:17]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 131731644HCID 131731644, compoundHCID 178418339Butyllithium

Product 1

HCID 131731643HCID 131731643, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

28.4 g of p-dibromobenzene was dissolved in diethyl ether, and 51.3 g n-butyl lithium was added to react with p-dibromobenzene at 0° C. Then, 31.2 g of (−)-pinanyldimethylsilyl chloride was added and reacted. A mixture obtained after a routine process was purified by distillation under reduced pressure to obtain 1-bromo-4-(−)-pinanyldimethylsilylbenzene. After dissolving 34.85 g of the obtained 1-bromo-4-(−)-pinanyldimethylsilylbenzene in diethyl ether, 42.4 g of n-butyl lithium and 6.9 g of dimethylformamide were successively added and the mixture was reacted. After processing by a routine method, the reaction mixture was purified by silica gel column chromatography to obtain 27.4 g of 4-(−)-pinanyldimethylsilylbenzaldehyde. After dissolving the obtained aldehyde in 200 ml of tetrahydrofuran, the solution was added to a solution of 36.9 g of methyltriphenyl iodide and 40.0 g of n-butyl lithium to obtain (−)-PSSt. The (−)-PSSt was purified by column chromatography using hexane as a developing solvent to obtain 15.0 g of purified (−)-PSSt. The structure was confirmed using NMR and IR.

Workup

  1. additionwere successively added
  2. customthe mixture was reacted
  3. customthe reaction mixture was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e8554cb5b64b4f268782b9ccc7573000
Source dataset
uspto-grants-2014_07
Patent number
US08764979B2

Reaction notes

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