Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 53950698, compound

HRID 1742742Notes

Reaction equation

HRID 1742742 reaction equation
[C:1]([N:4]1[C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([CH2:13][CH:14]=O)[C:7]=2[CH:6]=[CH: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>C1COCC1>[CH3:16][O:17][C:18](=[O:39])[CH:19]=[CH:14][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[CH:6]=[CH:5][N:4]2[C:1](=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 15050193HCID 15050193, compound

Product 1

HCID 53950698HCID 53950698, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-acetyl-indole-4-acetaldehyde (2.40 g, 11.93 mmol) prepared according to the method of H. Plieninger, et. al., Chem.Ber., 1956, 89:270 in THF (100 mL) was added methyl(triphenylphos-phoranylidene)acetate (4.78 g, 14.3 mmol). The solution was stirred at ambient temperature overnight. The solvent was removed in vacuo and the residue chromatographed (eluting with ethyl acetate/hexanes). Recrystallization from ethyl acetate/hexanes resulted in 2.12 g of the title compound as a white solid in two crops; MS(CI/NH3) m/e 258 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ2.60 (s, 3H), 3.70 (s, 3H), 3.75 (dd, 2H), 3.75 (m, 1H), 6.63 (dd, 1H), 7.05 (d, 1H), 7.12-7.22 (m, 2H), 7.29 (t, 1H), 7.43 (d, 1H), 8.35 (d, 1H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue chromatographed
  3. wash(eluting with ethyl acetate/hexanes)
  4. customRecrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b2b5bdc44b604728a2cf75eefc632991
Source dataset
uspto-grants-1994_08
Patent number
US05340802

Reaction notes

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