Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylate

HRID 2225802Notes

Reaction equation

HRID 2225802 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:17]([CH3:19])[CH3:18])[C:9]=2[CH:20]=O)=[CH:4][CH:3]=1.[C:22]([CH:26]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:24][CH3:25])=[O:23]>CO>[CH3:25][O:24][C:22](=[O:23])/[CH:26]=[CH:20]/[C:9]1[N:10]([CH:17]([CH3:18])[CH3:19])[C:11]2[C:16]([C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 113120613-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indole-2-carbaldehyde

Product 1

HCID 11221407methyl trans-3-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]acrylateYield 73.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

As in Example 226, the impure 3-(4-fluorophenyl)- 1-(1-methylethyl)-1H-indole-2-carboxaldehyde (5.56 g) from the previous example was reacted in methanol (75 mL) with (carbomethoxymethylene)triphenylphosphorane (6.2 g) was stirred at room temperature for 1 hour. The pale yellow solids that formed were filtered and washed with cold methanol to furnish 4.58 g of (E)-3-[3-(4-fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-2-propenoic acid methyl ester. A sample was crystallized from dichloromethane-hexane to yield the analytical specimen, mp 155°-157° C.

Workup

  1. customThe pale yellow solids that formed
  2. filtrationwere filtered
  3. washwashed with cold methanol

Sources & evidence

ORD record
ord-8e6b3823292a428a8999db4424e71fad
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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