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

HRID 2424941Notes

Reaction equation

HRID 2424941 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].[CH3:16][O:17][C:18](=[O:39])[CH:19]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:16][O:17][C:18](=[O:39])[CH2:19][C:6]1[C:7]2[C:12](=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:4]([C:1](=[O:3])[CH3:2])[CH:5]=1

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) 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-cbd1e306e5aa458f897e5702e3d3c903
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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