Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 19610404, compound

HRID 1602110Notes

Reaction equation

HRID 1602110 reaction equation
[C:1]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1C)=[CH:15][CH:14]=[CH:13][CH:12]=2)(=O)[C:2]1[CH:7]=CC=[CH:4][CH:3]=1.C(C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(OCC)=[O:20]>>[CH2:3](/[C:2](=[CH:1]\[C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)/[CH:7]=[O:20])[CH3:4]

Participants

3

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 616638HCID 616638, compound

Product 1

HCID 19610404HCID 19610404, compoundYield 39.4%

Conditions

Temperature
150 °C

Procedure

Ethyl (2E)-3-[2-(3-methylindolyl)]-3-phenyl-2-propenoate. A mixture of 2-benzoyl-3-methylindole (J. Org. Chem., 37, 3622 (1972)) (0.6 g, 2.55 mmol) and (carbethoxymethylene) triphenylphosphorane (2.1 g, 6 mmol) was heated at 150° C. in a sealed tube for 40 h. After cooling, the residue was chromatographed over silica gel (EtOAc/hexane 2:8) obtaining 0.2 g (25.7%) of the crude title compound as a solid, m.p.=125-130° C.

Workup

  1. temperatureAfter cooling
  2. customthe residue was chromatographed over silica gel (EtOAc/hexane 2:8)

Sources & evidence

ORD record
ord-96454dce0d4943a3a21bcedd7ea26845
Source dataset
uspto-grants-1999_11
Patent number
US05981525

Reaction notes

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