Tetrahydrofuran → 2-Ethoxycarbonyl-3-phenethyl-succinic acid diethyl ester

HRID 899071ノート

反応式

HRID 899071 の反応式
C([C:3](CC)([C:7]([O-:9])=[O:8])[C:4]([O-:6])=[O:5])C.[H-].[Na+].[CH2:14]([O:16][C:17](=[O:40])[CH:18](OS(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:15].CN1C(=O)N(C)[CH2:45][CH2:44]C1.[CH2:50]1COC[CH2:51]1>O>[CH2:50]([O:9][C:7](=[O:8])[CH:3]([C:4]([O:6][CH2:44][CH3:45])=[O:5])[CH:18]([CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:17]([O:16][CH2:14][CH3:15])=[O:40])[CH3:51]

参加物

7

反応物 5

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 69515632,2-DiethylpropanedioateHCID 140175682-(4-Nitro-benzenesulfonyloxy)-4-phenyl-butyric acid ethyl ester

生成物 1

HCID 536987412-Ethoxycarbonyl-3-phenethyl-succinic acid diethyl ester収率 52.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of diethylmalonate (240.2 mg, 1.5 mmol) and NaH (43.2 mg, 1.8 mmol) in THF (3 ml) was stirred for one hour at room temperature under argon. 2-(4-Nitro-benzenesulfonyloxy)-4-phenyl-butyric acid ethyl ester (590 mg, 1.5 mmol) and DMPU (192.2 mg, 1.5 mmol) was added and the mixture was stirred at room temperature for three days. The reaction was poured into H2O and extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure. The product was purified by column chromatography (petroleumether/ethyl acetate, 4:1) to give 2-ethoxycarbonyl-3-phenethyl-succinic acid diethyl ester (274 mg, 52.1%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. concentrationconcentrated under reduced pressure
  4. customThe product was purified by column chromatography (petroleumether/ethyl acetate, 4:1)

出典と根拠

ORDレコード
ord-2d3f5065d0644036997ed11b400c7493
出典データセット
uspto-grants-2008_04
特許番号
US07354895B1

反応ノート

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