trans-2-Benzyl-3-[2-(4-methoxy-phenyl)-vinyl]-benzo[b]thiophene → 2-Benzyl-3-[2-(4-methoxy-phenyl)-ethyl]-benzo[b]thiophene

HRID 1280903Notes

Reaction equation

HRID 1280903 reaction equation
[CH2:1]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[CH2:1]([C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 23445619trans-2-Benzyl-3-[2-(4-methoxy-phenyl)-vinyl]-benzo[b]thiophene

Product 1

HCID 234456642-Benzyl-3-[2-(4-methoxy-phenyl)-ethyl]-benzo[b]thiophene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

At ambient temperature, a mixture of cis and trans-2-benzyl-3-[2-(4-methoxy-phenyl)-vinyl]-benzo[b]thiophene in EtOAc and 10% palladium on carbon was stirred under H2 (atmospheric conditions). The reaction was filtered and the filtrate concentrated to give the title compound as a white solid, mp 68-70° C. 1H NMR; consistent. mass spectrum (EI) m/z 358 (M+). Anal. Calcd. for C24H22OS: C, 80.41; H, 6.19; N, 0.00. Found: C, 80.20; H, 6.18; N, 0.03.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-c8e2af041f0a4dea942c9cee0bceb360
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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