Sodium Chloride → 2-Acetyl-2-propyl-succinic acid diethyl ester

HRID 1244258Notes

Reaction equation

HRID 1244258 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:12](=[O:14])[CH3:13])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[H-].[Na+].[CH2:18](I)[CH2:19][CH3:20].[Na+].[Cl-]>CS(C)=O.O>[CH2:1]([O:3][C:4](=[O:15])[C:5]([C:12](=[O:14])[CH3:13])([CH2:18][CH2:19][CH3:20])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 66197Butanedioic acid, 2-acetyl-, 1,4-diethyl ester

Product 1

HCID 596930242-Acetyl-2-propyl-succinic acid diethyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2-acetyl-succinic acid diethyl ester (30 g, 139 mmol) in DMSO (250 ml) is added NaH (5.8 g, 60% in mineral oil, 145 mmol) in 10 portions over a period of 1 hour. The resulting solution is stirred at room temperature for another 1.5 hours. PrI (17.1 ml, 174 mmol) is added slowly over the period of 45 minutes and the resulting solution is stirred at room temperature overnight. Water (500 ml) is added, the solution is saturated with NaCl and extracted with EtOAc (3×250 ml). The combined extracts are washed with brine (400 ml), dried over Na2SO4 and evaporated in vacuo. The resulting 2-acetyl-2-propyl-succinic acid diethyl ester is obtained as a yellow oil, which is used for the next step without further purification.

Workup

  1. stirringthe resulting solution is stirred at room temperature overnight
  2. extractionextracted with EtOAc (3×250 ml)
  3. washThe combined extracts are washed with brine (400 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-365857c607524c878919b0985ee42189
Source dataset
uspto-grants-2006_10
Patent number
US07122546B2

Reaction notes

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