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

HRID 899071노트

반응식

HRID 899071 반응식
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]

참가 물질

7

반응물 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

생성물 1

HCID 536987412-Ethoxycarbonyl-3-phenethyl-succinic acid diethyl ester수율 52.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-2d3f5065d0644036997ed11b400c7493
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354895B1

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