Hydrochloric Acid → Diethyl 2-[1-(2,4-dimethoxyphenyl)hexyl]malonate

HRID 1418170Notes

Reaction equation

HRID 1418170 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH2:23]([Mg]Br)[CH2:24][CH2:25][CH2:26][CH3:27].Cl>C(OCC)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]([CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10757178Ethyl 3-(2,4-dimethoxyphenyl)-2-ethoxycarbonyl-2-propenoateHCID 178445865HCID 178445865, compound

Product 1

HCID 19348766Diethyl 2-[1-(2,4-dimethoxyphenyl)hexyl]malonateYield 77%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 9.15 g (29.7 mmol) of ethyl 3-(2,4-dimethoxyphenyl)-2-ethoxycarbonyl-2-propenoate (prepared as described in Preparation 1) in 9 ml of diethyl ether was added to 72 ml (36 mmol) of a 0.5M ice-cooled solution of pentylmagnesium bromide in diethyl ether, and the resulting mixture was stirred at the same temperature for 1.5 hours. At the end of this title, the reaction mixture was poured into a 10% aqueous solution of hydrochloric acid in ice, and then extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 200 g of silica gel, using a 10:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 8.65 g (yield 77%) of the title compound as an oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through 200 g of silica gel
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-2039fa01a71443418596504392af8c44
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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