Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 86711434, compound

HRID 1401091Notes

Reaction equation

HRID 1401091 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]=O.[CH2:13]([O:15][C:16](=[O:37])[CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:14]>C1C=CC=CC=1>[CH2:13]([O:15][C:16](=[O:37])/[CH:17]=[CH:11]/[C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=2)[NH:7][CH:6]=1)[CH3:14]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 2591875-Methylindole-3-carboxaldehyde

Product 1

HCID 86711434HCID 86711434, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

5-methyl-1H-indole-3-carbaldehyde (900 mg, 5.65 mmol) was dissolved in benzene (100 ml), and ethyl(Triphenylphosphoranylidene)acetate (2954.1 mg, 8.48 ml) was drop-wise added. The temperature of mixture was raised to 80° C. and stirred under reflux for 12 hr. After completion of the reaction, the reaction mixture was cooled to room temperature, concentrated under reduced pressure, and refined through silica gel chromatography (n-hexane:EtOAc=4:1) to give target compound (1230 mg, 95%).

Workup

  1. temperatureunder reflux for 12 hr
  2. customAfter completion of the reaction
  3. temperaturethe reaction mixture was cooled to room temperature
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-84ce9278607846949e8862872090a424
Source dataset
uspto-grants-2014_12
Patent number
US08906952B2

Reaction notes

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