Acetonitrile → HCID 54186988、化合物

HRID 654980ノート

反応式

HRID 654980 の反応式
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]

参加物

5

反応物 3

HCID 6342Acetonitrile2 回HCID 13338668Magnesium mono-p-nitrobenzyl malonateHCID 178438938HCID 178438938、化合物

生成物 1

HCID 54186988HCID 54186988、化合物

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ca132e0b481649239ecc848cdd28266b
出典データセット
uspto-grants-1992_07
特許番号
US05134231

反応ノート

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