Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 1,1-dimethylethyl hexahydro-2-(4-methoxy-4-oxo-2-butenyl)-7-oxo-1H-azepine-1-carboxylate

HRID 849142Notes

Reaction equation

HRID 849142 reaction equation
O=[CH:2][CH2:3][CH:4]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6](=[O:11])[N:5]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C1(P(=[CH:38][C:39]([O:41][CH3:42])=[O:40])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:42][O:41][C:39](=[O:40])[CH:38]=[CH:2][CH2:3][CH:4]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6](=[O:11])[N:5]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 18800797HCID 18800797, compound

Product 1

HCID 542261121,1-dimethylethyl hexahydro-2-(4-methoxy-4-oxo-2-butenyl)-7-oxo-1H-azepine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Example 209) The crude aldehyde of this Example, part B above, is dissolved in toluene and treated with 1.2 equivalents of methyl (triphenylphosphoranylidene)acetate. The mixture is refluxed for four hours. After cooling, the mixture is concentrated and the residue is triturated with several volumes of pentane to remove the phosphorous salts. The extracts are filtered and stripped of all solvent. The crude residue is then purified by column chromatography to give the title product.

Workup

  1. temperatureThe mixture is refluxed for four hours
  2. temperatureAfter cooling
  3. concentrationthe mixture is concentrated
  4. customthe residue is triturated with several volumes of pentane
  5. customto remove the phosphorous salts
  6. filtrationThe extracts are filtered
  7. customThe crude residue is then purified by column chromatography

Sources & evidence

ORD record
ord-fe4b3241720041b6ba1722019e78519c
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Reaction notes

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