Hydrochloric Acid → HCID 10960547, compound

HRID 1873227Notes

Reaction equation

HRID 1873227 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].[C:29]([O:35][CH3:36])(=[O:34])[CH2:30][C:31]([CH3:33])=[O:32].Cl>CS(C)=O>[C:31]([CH:30]([C:29]([O:35][CH3:36])=[O:34])[C:2]1[CH:3]=[C:4]([C:11]([CH3:22])([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])(=[O:32])[CH3:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 11430Potassium CarbonateHCID 12854241Propanedioic acid, 2-(3-chloro-4-nitrophenyl)-2-methyl-, 1,3-diethyl ester

Product 1

HCID 10960547HCID 10960547, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of diethyl 2-(3-chloro-4-nitrophenyl)-2-methylmalonate (1.0 g, 3.03 mmol.) in dimethyl sulfoxide (DMSO, 3mL) were added potassium carbonate (1.25 g, 9.09 mmol.) and methyl acetoacetate (0.99 mL, 9.0 mmol.). The resulting mixture was stirred at 70° C. for 6 hours. The reaction mixture was cooled to room temperature, neutralized with diluted hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate portion was washed with an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. The dried portion was concentrated to leave a residue. The residue was purified by silica gel column chromatography (Wako Gel C-330, available from Wako Jyunyaku Industry Co., Ltd., toluene/ethyl acetate=100/4, v/v), to give 0.64 g (yield: 52%) of the desired compound as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate portion was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe dried portion was concentrated
  6. customto leave a residue
  7. customThe residue was purified by silica gel column chromatography (Wako Gel C-330, available from Wako Jyunyaku Industry Co., Ltd., toluene/ethyl acetate=100/4, v/v)

Sources & evidence

ORD record
ord-cb7dc4cca6a847d4a69e9acb83382314
Source dataset
uspto-grants-2000_08
Patent number
US06111115

Reaction notes

Loading…