Methyl 4-Formylbenzoate → Methyl 4-[(3-Trimethylsilylphenyl)ethenyl]benzoate

HRID 466326Notes

Reaction equation

HRID 466326 reaction equation
[Br-].[CH3:2][Si:3]([CH3:13])([CH3:12])[C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7][PH3+].[CH:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=O.C[O-].[Na+].CO>CO>[CH3:2][Si:3]([CH3:13])([CH3:12])[C:4]1[CH:5]=[C:6]([CH:7]=[CH:14][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 19591670(m-Trimethylsilylbenzyl)phosphonium bromideHCID 23694274Sodium methanolate methanol

Product 1

HCID 53854108Methyl 4-[(3-Trimethylsilylphenyl)ethenyl]benzoateYield 24.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(m-Trimethylsilylbenzyl)phosphonium bromide (758 mg, 1.50 mmol) and methyl 4-formylbenzoate (258 mg, 1.57 mmol) were added to a NaOMe-methanol solution, which was prepared from 40 mg (1.74 mmol) of Na metal and 15 ml of dry methanol, and the mixture was stirred for 17 hours. The precipitate (trans form) was collected by filtration, washed with a cooled mixture of MeOH and n-hexane, and dried in vacuo to give 115 mg of white crystals. The mother liquors were evaporated and dissolved in CH2Cl2. The insoluble substance was filtered off and the filtrate was evaporated. The residue was purified by column chromatography to give 60 mg of colorless oil (cis form, yield 13%), 158 mg of white crystals (trans form, total yield 59%) and 110 mg of interfraction (yield 23%).

Workup

  1. filtrationThe precipitate (trans form) was collected by filtration
  2. washwashed with a cooled mixture of MeOH and n-hexane
  3. customdried in vacuo

Sources & evidence

ORD record
ord-bd79186bc1734127976d0ba92c2d091f
Source dataset
uspto-grants-1992_10
Patent number
US05155249

Reaction notes

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