(Triphenylphosphoranylidene)acetaldehyde → HCID 14358692, compound

HRID 1602107Notes

Reaction equation

HRID 1602107 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:10]=O.[CH:12]([CH:14]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13]>C1(C)C=CC=CC=1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1/[CH:10]=[CH:14]/[CH:12]=[O:13]

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 96389Indole-2-carboxaldehyde

Product 1

HCID 14358692HCID 14358692, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Indole 2-carboxaldehyde (6.72 g, 46.3 mmol) was dissolved in dry toluene (450 ml) and treated with (formylmethylene)triphenylphosphorane (21.3 g, 70 mmol). The reaction mixture was treated under reflux for 4 h, allowed to cool and chromatographed over silica gel using toluene (2×500 ml) and then hexane/EtOAc (3:1) (2×500 ml) as the eluent. Evaporation of the solvent and recrystallization of the residue from toluene yielded 4.96 g (62.6%) of the title compound, m.p.=203-204° C.

Workup

  1. additionThe reaction mixture was treated
  2. temperatureunder reflux for 4 h
  3. temperatureto cool
  4. customchromatographed over silica gel
  5. customEvaporation of the solvent and recrystallization of the residue from toluene

Sources & evidence

ORD record
ord-40a013017d2a4ba98e5b39a0d74348a8
Source dataset
uspto-grants-1999_11
Patent number
US05981525

Reaction notes

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