Toluene → Ethyl 4-(3-isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-cinnamate

HRID 1007508Notes

Reaction equation

HRID 1007508 reaction equation
[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][C:17](C=O)=[CH:16][C:15]=3[C:26]([F:29])([F:28])[F:27])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2].[CH2:30]([O:32][C:33]([CH:35]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:34])[CH3:31].[C:55]1(C)C=CC=CC=1>>[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:15]([C:26]([F:27])([F:29])[F:28])=[CH:16][C:17]([CH:55]=[CH:35][C:33]([O:32][CH2:30][CH3:31])=[O:34])=[CH:20][C:21]=3[C:22]([F:24])([F:25])[F:23])[CH:11]=2)[NH:6][CH:5]=1)([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 1140TolueneHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 226698054-(3-Isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-benzaldehyde

Product 1

HCID 86587749Ethyl 4-(3-isopropyl-1H-indol-5-yloxy)-3,5-bis-trifluoromethyl-cinnamate

Procedure

1.0 g (2.41 mmol) of aldehyde derivative from Example V is dissolved in 10 ml of toluene and 0.92 g (2.65 mmol) of ethoxycarbonylmethylene-triphenylphosphorane is introduced in portions. After stirring at room temperature for 2 days, the reaction mixture is concentrated to a half of the volume and chromatographed on silica gel 60 by means of toluene.

Workup

  1. concentrationthe reaction mixture is concentrated to a half of the volume
  2. customchromatographed on silica gel 60 by means of toluene

Sources & evidence

ORD record
ord-c0f03b9626f148c987865856a4079ec3
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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