Water → 2, 3-Dimethoxybenzyl-n-pentylmalonic acid diethyl ester

HRID 1756765ノート

反応式

HRID 1756765 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:18])[CH:7]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4].[CH3:19][O:20][C:21]1[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Cl.O>CN(C)C=O>[CH2:3]([O:5][C:6](=[O:18])[C:7]([CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[C:28]([O:29][CH3:30])[C:21]=1[O:20][CH3:19])([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:4]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 80167Diethyl pentylmalonateHCID 27583941-(Chloromethyl)-2,3-dimethoxybenzene

生成物 1

HCID 540695252, 3-Dimethoxybenzyl-n-pentylmalonic acid diethyl ester収率 73.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

To a suspension of 60% sodium hydride (440 mg, 11 mmol) in 5 ml of dimethylformamide was added a solution of 2.30 g (10 mmol) of n-pentylmalonic acid diethyl ester in 5 m of dimethylformamide under stirring and ice cooling, and the resultant mixture was stirred for 30 minutes. A solution of 1.86 g (10 mmol) of 2, 3-dimethoxybenzyl chloride in 5 ml of dimethylformamide was dropwise added to the mixture, which was stirred at 70° C. for 1 hour. After cooling, the reaction mixture was mixed with water and extracted with ethyl acetate. The organic layers were combined, washed with water and saturated saline in this order, dried over anhydrous magnesium sulfate and the solvent evaporated in vacuo. The residue was chromatographed on a silica gel column, eluting with ethyl acetate/hexane (1/12) to give 2.78 g of 2, 3-dimethoxybenzyl-n-pentylmalonic acid diethyl ester as a colorless oil. Yield, 73%.

後処理

  1. stirringwas stirred at 70° C. for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. washwashed with water and saturated saline in this order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent evaporated in vacuo
  7. customThe residue was chromatographed on a silica gel column
  8. washeluting with ethyl acetate/hexane (1/12)

出典と根拠

ORDレコード
ord-c46aebd1d2a04dbe9019a4ac1edbddb4
出典データセット
uspto-grants-1995_08
特許番号
US05442060

反応ノート

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