Acrylonitrile → HCID 67158683, compound

HRID 549400Notes

Reaction equation

HRID 549400 reaction equation
[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][NH:13]2)=[CH:8][CH:7]=1.[C:18](#[N:21])[CH:19]=[CH2:20]>>[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:20][CH2:19][C:18]#[N:21])=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 7855AcrylonitrileHCID 57899223HCID 57899223, compound

Product 1

HCID 67158683HCID 67158683, compoundYield 98.1%

Procedure

A mixture of (E)-3-(4-pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester (1.0 g, 4.3 mmol), acrylonitrile (1.1 g, 22 mmol) and silica gel (4 g, grade 62 60-200 mesh 150 Å) was stirred at room temperature for 24 h. The reaction mixture was purified via silica gel column chromatography to give (E)-3-{4-[1-(2-cyano-ethyl)-pyrrolidin-2-yl]-phenyl}-acrylic acid methyl ester (1.2 g, 98%) as a colorless oil. LCMS (m/z): 285.1 (M+1).

Workup

  1. customThe reaction mixture was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-2b0152f38feb449eb44c37f00b6fb29f
Source dataset
uspto-grants-2011_05
Patent number
US07943652B2

Reaction notes

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