Water → HCID 19390157, compound

HRID 1757273Notes

Reaction equation

HRID 1757273 reaction equation
[Br-].[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].[H-].[Na+].[S:29]1[CH:33]=[CH:32][C:31]([C:34]2[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=2)[CH:37]=O)=[CH:30]1.O>CN(C)C=O.C(O)(=O)C>[C:2]([CH2:4][CH2:5][CH2:6]/[CH:7]=[CH:37]/[C:36]1[CH:35]=[C:34]([C:31]2[CH:32]=[CH:33][S:29][CH:30]=2)[CH:41]=[CH:40][CH:39]=1)#[N:3]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 45475263-(Thiophen-3-yl)benzaldehydeHCID 11418829(4-Cyanobutyl)(triphenyl)phosphanium bromide

Product 1

HCID 19390157HCID 19390157, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

44.6 g of 4-cyanobutyl(triphenyl)phosphonium bromide is suspended in 250 ml of dimethylformamide, 4.2 g of 60% oily sodium hydride is added under ice cooling and stirring, the mixture is stirred at that temperature for 30 minutes, 18 g of 3-(3-thienyl)benzaldehyde is added, and the mixture is stirred at room temperature for 20 hours. Water and acetic acid are added to the reaction solution for neutralization, the solvent is distilled off under reduced pressure, and the residue is post-treated in a conventional manner and purified by silica gel column chromatography [Wako gel C-100, 500 g; hexane/ethyl acetate=5/1] to obtain 23.2 g of (E)-3-[3-(5-cyano-1-pentenyl)phenyl]thiophene as colorless oil.

Workup

  1. stirringthe mixture is stirred at that temperature for 30 minutes
  2. stirringthe mixture is stirred at room temperature for 20 hours
  3. distillationthe solvent is distilled off under reduced pressure
  4. additionthe residue is post-treated in a conventional manner
  5. custompurified by silica gel column chromatography [Wako gel C-100, 500 g; hexane/ethyl acetate=5/1]

Sources & evidence

ORD record
ord-957ecab288764102a76686b5d4bdb67c
Source dataset
uspto-grants-1995_08
Patent number
US05444084

Reaction notes

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