Tetrahydrofuran → HCID 67787979, compound

HRID 1757272Notes

Reaction equation

HRID 1757272 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=2)[CH:9]=O)=[CH:2]1.[Br-].[CH3:15][O:16][C:17]([C:19]1[CH:20]=[C:21]([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:22]=[CH:23][CH:24]=1)=[O:18].O1CCC[CH2:45]1.[H-].[Na+]>C(O)(=O)C.CN(C)C=O>[CH3:15][O:16][C:17](=[O:18])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21](/[CH:45]=[CH:9]\[C:8]2[CH:11]=[CH:12][CH:13]=[C:6]([C:3]3[CH:4]=[CH:5][S:1][CH:2]=3)[CH:7]=2)[CH:20]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 45475263-(Thiophen-3-yl)benzaldehydeHCID 86748938HCID 86748938, compound

Product 1

HCID 67787979HCID 67787979, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

1.88 g of 3-(3-thienyl)benzaldehyde and 5.9 g of 3-methoxycarbonylphenyl(triphenyl)phosphonium bromide are added to a mixture of 60 ml of tetrahydrofuran and 6 ml of dimethylformamide, 0.48 g of 60% oily sodium hydride is added under ice cooling and stirring, and the mixture is stirred at room temperature for 6 hours. The reaction solution is neutralized with acetic acid, the solvent is distilled off under reduced pressure, and the residue is extracted with a system of water and methylene chloride. The organic layer is post-treated in a conventional manner, and the product is purified by silica gel column chromatography [Wako gel C-200, 60 g; hexane/ethyl acetate=10/1] to obtain 1.24 g (Z)-3-[2-[3-(3-thienyl)phenyl]ethenyl]benzoic acid methyl ester as a white crystalline solid.

Workup

  1. additionis added under ice cooling
  2. stirringthe mixture is stirred at room temperature for 6 hours
  3. distillationthe solvent is distilled off under reduced pressure
  4. extractionthe residue is extracted with a system of water and methylene chloride
  5. additionThe organic layer is post-treated in a conventional manner
  6. customthe product is purified by silica gel column chromatography [Wako gel C-200, 60 g; hexane/ethyl acetate=10/1]

Sources & evidence

ORD record
ord-49e74ff2f0134c4e8a1ca64cb90984ff
Source dataset
uspto-grants-1995_08
Patent number
US05444084

Reaction notes

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