Acetonitrile → HCID 54186988, compound

HRID 654980Notes

Reaction equation

HRID 654980 reaction equation
CC(CC1C=CC=CC=1)C(O)=[S:4].[Mg+2].[N+:14]([C:17]1[CH:30]=[CH:29][C:20]([CH2:21][O:22][C:23](=O)[CH2:24][C:25]([O-:27])=O)=[CH:19][CH:18]=1)([O-:16])=[O:15].C(O[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([N+]([O-])=O)=[CH:41][CH:40]=1)(=O)CC([O-])=O.[C:48](#N)[CH3:49]>C(OCC)(=O)C>[O:27]=[C:25]([CH:48]([CH3:49])[CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:24][C:23]([O:22][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:30][CH:29]=1)=[S:4]

Participants

5

Reactant 3

HCID 6342Acetonitrile2×HCID 1333866883972-01-4HCID 178438938HCID 178438938, compound

Product 1

HCID 54186988HCID 54186988, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-Methyl-3-phenylthiopropionic acid (4.60 g; 23.44 mmole) was dissolved in dry acetonitrile (20 ml), and 1,1-carbonyldiimidazole (4.56 g; 28.13 mmole) was added thereto with ice-cooling, and the resultant mixture was stirred at the same temperature for 30 minutes. The reaction mixture was dropwise added to a solution of malonic acid p-nitrobenzyl ester magnesium salt (17.53 g; 35 mmole) in dry acetonitrile (70 ml) at 50° C., and the resultant mixture was stirred at the same temperature for 30 minutes. After completion of the reaction, the reaction mixture was returned to room temperature and diluted with ethyl acetate. The organic layer was washed successively with lN hydrochloric acid, water, a saturated sodium bicarbonate solution, water and an aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give p-nitrobenzyl 3-oxo-4-methyl-5-phenylthiopentanoate.

Workup

  1. temperaturewith ice-cooling
  2. customAfter completion of the reaction
  3. customwas returned to room temperature
  4. washThe organic layer was washed successively with lN hydrochloric acid, water
  5. dry with materiala saturated sodium bicarbonate solution, water and an aqueous sodium chloride solution and dried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-ca132e0b481649239ecc848cdd28266b
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

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