Acetate → HCID 11139204, compound

HRID 655894Notes

Reaction equation

HRID 655894 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[CH:13]=O.[C:15]([O-:18])(=[O:17])[CH3:16].[CH:19]1C=CC=CC=1>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[CH:13]=[CH:16]/[C:15]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 3

HCID 175AcetateHCID 241BenzeneHCID 6479252HCID 6479252, compound

Product 1

HCID 11139204HCID 11139204, compoundYield 56%

Procedure

A solution of (E)-3-(2-quinolinyl)-2-propenal (23) and methyl (triphenylphrophoranylidene) acetate (1.10 g, 3.27 mmol) in benzene (15 ml) was stirred for 6 hours at room temperature. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel with diethyl ether-petrol ether (1:2) as eluent to give the title compound (0.44 g, 56%). 1H NMR (DMSO-d6, HMDSO), δ: 3.72 (3H, s); 6.32 (1H, d, J=16.0 Hz); 7.45 (1H, d, J=10.0 Hz); 7:52-4.85 (5H, m); 7.85-7.18 (2H, m); 8.35 (1H, d, J=9.0 Hz).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel with diethyl ether-petrol ether (1:2) as eluent

Sources & evidence

ORD record
ord-48020b37f9a8423c88f0eb9a5de6f8ca
Source dataset
uspto-grants-2011_12
Patent number
US08071620B2

Reaction notes

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