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

HRID 29769Notes

Reaction equation

HRID 29769 reaction equation
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]

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-27d87e6a1c7e42e880e9084aec83c160
Source dataset
uspto-grants-2008_09
Patent number
US07423012B2

Reaction notes

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