Toluene → 3-(1-benzenesulfonyl-1H-indol-5-yl)-acrylic acid methyl ester

HRID 1716779Notes

Reaction equation

HRID 1716779 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15](C=O)=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][O:22][C:23](=[O:44])[CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[C:45]1(C)C=CC=CC=1>>[CH3:21][O:22][C:23](=[O:44])[CH:24]=[CH:45][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:10]([S:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:8])=[O:9])[CH:11]=[CH:12]2

Participants

4

Reactant 3

HCID 1140TolueneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 177503871-(benzenesulfonyl)-1H-indole-5-carbaldehyde

Product 1

HCID 673571463-(1-benzenesulfonyl-1H-indol-5-yl)-acrylic acid methyl ester

Conditions

Temperature
110 °C

Procedure

A mixture of 1-benzenesulfonyl-1H-indole-5-carbaldehyde CCKXIV (3.671 g, 12.866 mmol) and methyl(triphenylphosphoranylidene)acetate (5.38 g, 16.082 mmol) in toluene (80 mL) was heated to 110° C. for 68 hours. The resulting mixture was concentrated under reduced pressure and the crude residue was purified by flash chromatography (EtOAc/hexane, 20/80 to 35/65) to afford 4.479 g of 3-(1-benzenesulfonyl-1H-indol-5-yl)-acrylic acid methyl ester CCLXV as a white solid in a mixture 10/1 of (E) and (Z) diastereomers.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. customthe crude residue was purified by flash chromatography (EtOAc/hexane, 20/80 to 35/65)

Sources & evidence

ORD record
ord-0208c1ee88eb49808672d8f510e3388e
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

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