Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 57845369, compound

HRID 734397Notes

Reaction equation

HRID 734397 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6](=O)[CH2:5]1)(=[O:3])[CH3:2].C1(P(=[CH:35][C:36]([O:38][CH3:39])=[O:37])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6]([CH2:35][C:36]([O:38][CH3:39])=[O:37])=[CH:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 12477809HCID 12477809, compound

Product 1

HCID 57845369HCID 57845369, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-acetyl-6-methoxy-1,2-dihydro-3H-indol-3-one (3.96 g, 19.3 mmol) (Example 12) and methyl (triphenylphosphoranylidene)acetate (19.75 g, 57.9 mmol) in toluene (60 mL) was heated at reflux under argon for 24 h. The mixture was loaded on silica gel and eluted with EtOAc/hexane (1/5) to yield a thick oil (2.52 g, 50%). LC/MS m/z 262 (M+H)+; 1H NMR (400 MHz, CDCl3) δ 8.04 (br s, 1H), 7.38 (d, 1H), 7.31 (s, 1H), 6.92 (dd, 1H), 3.89 (s, 3H), 3.74 (s, 3H), 3.71 (d, 2H), 2.62 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon for 24 h
  3. washeluted with EtOAc/hexane (1/5)

Sources & evidence

ORD record
ord-d34f60c7cd5941d99c34cb677a3c482a
Source dataset
uspto-grants-2009_09
Patent number
US07592361B2

Reaction notes

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