(Triphenylphosphoranylidene)acetaldehyde → 3-Cyano-6-((4-methoxybenzyl)oxy)-1-(2-formylethenyl)benzene

HRID 1700286Notes

Reaction equation

HRID 1700286 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH:6]=O)#[N:2].C1(P(=[CH:40][CH:41]=[O:42])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:40][CH:41]=[O:42])[C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)#[N:2]

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 183181563-Cyano-6-((4-methoxybenzyl)oxy)benzaldehyde

Product 1

HCID 734371553-Cyano-6-((4-methoxybenzyl)oxy)-1-(2-formylethenyl)benzeneYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-cyano-6-((4-methoxybenzyl)oxy)benzaldehyde (2.8 g) and (triphenylphosphoranylidene)acetaldehyde (3.5 g) in 40 mL CH2Cl2 was stirred at reflux for 16 hours. The solution was cooled to ambient temperature, concentrated and purified on silica gel column (ethyl acetate/hexane/CH2Cl2, 1:8:3) to give 3-cyano-6-((4-methoxybenzyl)oxy)-1-(2-formylethenyl)benzene (2.8 g) as a yellow solid.

Workup

  1. temperatureat reflux for 16 hours
  2. concentrationconcentrated
  3. custompurified on silica gel column (ethyl acetate/hexane/CH2Cl2, 1:8:3)

Sources & evidence

ORD record
ord-f7956ba48ff845eba8f2c1eccbc4165e
Source dataset
uspto-grants-2002_02
Patent number
US06350761B1

Reaction notes

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