(Triphenylphosphoranylidene)acetaldehyde → (E)-3-(5-methoxy-2-indolyl)-2-propenaldehyde

HRID 1602108

Reaction equation

HRID 1602108 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH:12]=O)=[CH:6]2.[CH:14]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:15]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](/[CH:12]=[CH:16]/[CH:14]=[O:15])=[CH:6]2

Participants

4

Reactant 2

HCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 8264565-Methoxy-1H-indole-2-carbaldehyde

Product 1

HCID 19610401(E)-3-(5-methoxy-2-indolyl)-2-propenaldehydeYield 26.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

5-Methoxyindole-2-carboxaldehyde (1.5 g, 8.5 mmol) was dissolved in dry toluene (30 ml) and treated with (formylmethylene)triphenylphosphorane (3 g, 9.8 mmol). The reaction mixture was stirred at 85° C. for 5 h, allowed to cool and chromatographed over silica gel using hexane/EtOAc (7:3). Evaporation of the solvent yielded 0.45 g (26 %) of (E)-3-(5-methoxy-2-indolyl)-2-propenaldehyde, m.p.=145-147° C.

Workup

  1. temperatureto cool
  2. customchromatographed over silica gel
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-73d513385919411a8ac8170bcc619bbe
Source dataset
uspto-grants-1999_11
Patent number
US05981525

Linked notes

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