Toluene → HCID 54298386, compound

HRID 1451517Notes

Reaction equation

HRID 1451517 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9](C=O)=[C:8]2[CH3:20])=[CH:4][CH:3]=1.[C:23]([CH:28]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:25][CH2:26][CH3:27])=[O:24].[C:48]1(C)C=CC=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([CH:48]=[CH:28][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:8]2[CH3:20])=[CH:21][CH:22]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 19974927HCID 19974927, compound

Product 1

HCID 54298386HCID 54298386, compound

Procedure

A mixture of the indole from Step 2 (8.46 g, 23.6 mmol) and (carbethoxymethylene)triphenylphosphorane (16.9 g, 48.6 mmol) was suspended in 25 mL of toluene and heated to reflux for 15 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (25% ethyl acetate/hexanes) to provide 9.38 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for 15 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by flash chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a3ed86b9d21f46eb89e575d344680571
Source dataset
uspto-grants-1997_02
Patent number
US05604253

Reaction notes

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