Tetrahydrofuran → HCID 86752814, compound

HRID 964416Notes

Reaction equation

HRID 964416 reaction equation
[Br-].[Cl:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[C:29](OC)=O)C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:33]([C:35]1[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=1)=O.[CH3:45][O-:46].[Na+].[O:48]1CCC[CH2:49]1>>[Cl:2][C:3]1[CH:4]=[C:5]([C:45]([O:48][CH3:49])=[O:46])[CH:26]=[CH:27][C:28]=1/[CH:29]=[CH:33]/[C:35]1[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 15294Methyl 4-FormylbenzoateHCID 10942334Sodium MethoxideHCID 19080054HCID 19080054, compound

Product 1

HCID 86752814HCID 86752814, compound

Procedure

A suspension of 52.6 g of (3-chloro-4-methoxycarbonyl-benzyl)-triphenylphosphonium bromide and 16.4 g of methyl 4-formyl-benzoate in 700 ml of tetrahydrofuran was treated dropwise within 30 minutes with 115 ml of a 2% sodium methanolate solution and the mixture was stirred at room temperature for 1 hour. The reaction mixture was suction filtered. The filtrate was concentrated and the residue was chromatographed over silica gel with ethyl acetate/hexane/methylene chloride to give colorless crystals of dimethyl (E)-2-chloro-stilbene-4,4'-dicarboxylate, MS: m/z 330.0 (M+).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customthe residue was chromatographed over silica gel with ethyl acetate/hexane/methylene chloride

Sources & evidence

ORD record
ord-2fb586008e2a40d6bf499f94e74f0dd2
Source dataset
uspto-grants-1998_06
Patent number
US05767268

Reaction notes

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