Benzenepropanal → HCID 5368481, compound

HRID 1457717Notes

Reaction equation

HRID 1457717 reaction equation
[CH:1](=O)[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:11][O:12][C:13](=[O:34])[CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[C:4]1([CH2:3][CH2:2]/[CH:1]=[CH:14]/[C:13]([O:12][CH3:11])=[O:34])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7707BenzenepropanalHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester

Product 1

HCID 5368481HCID 5368481, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of hydrocinnamaldehyde (13.42 g, 0.1 mol) and methyl(triphenylphosphoranylidene)acetate (33.44 g, 0.1 mol) in THF was stirred at reflux for 20 hours. The reaction mixture was concentrated under vacuum and the residue was purified by flash chromatography using hexane:EtOAc::9:1. The desired product was obtained as a clear, pale yellow oil (8.0 g, 0.042 mol, 42%); 1H NMR (300 MHz, CDCl3) δ 7.3-7.2 (m, 2H), 7.2-7.1 (m, 3H), 7.1-6.9 (m, 1H), 5.85 (d, 1H, J=5.8 Hz), 3.75 (s, 3H), 2.8 (t, 2H, J=7.7 Hz), 2.55 (q, 2H, J=7.4 Hz); MS (NH3 -DCI) 191 (M+H)+.

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-30ab42a9bf7c4aeb98bb1d1d3ae12491
Source dataset
uspto-grants-1998_12
Patent number
US05849736

Reaction notes

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