Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 273732, compound

HRID 1725324Notes

Reaction equation

HRID 1725324 reaction equation
[C:1]1(=[O:16])[N:5]([CH2:6][CH2:7][CH2:8][CH:9]=O)[C:4](=[O:11])[C:3]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]12.[CH3:17][O:18][C:19](=[O:40])[CH:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl>[CH3:17][O:18][C:19](=[O:40])[CH:20]=[CH:9][CH2:8][CH2:7][CH2:6][N:5]1[C:4](=[O:11])[C:3]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:2]2[C:1]1=[O:16]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal

Product 1

HCID 273732HCID 273732, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Phthalimidobutanal (120.9 g, 556 mmol) was then dissolved in 600 ml of CH2Cl2 and treated with methyl(triphenylphosphoranylidene)acetate (186 g, 556 mmol) in 600 ml of CH2Cl2. After 1 h the mixture was concentrated in vacuo and chromatographed in seven equal portions (Merck Kieselgel 60; 7×14 cm column; eluent 30% ethyl acetate in hexane) to give 145.6 g (96%) of methyl-6-phtalimidohex-2-enoate as a white solid.

Workup

  1. concentrationAfter 1 h the mixture was concentrated in vacuo
  2. customchromatographed in seven equal portions (Merck Kieselgel 60; 7×14 cm column; eluent 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b0e712ed96bc4ecd9c2d7d65781d4d2b
Source dataset
uspto-grants-2009_02
Patent number
US07491520B2

Reaction notes

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