Diethyl (ethoxymethylene)malonate → HCID 59255053, compound

HRID 639537Notes

Reaction equation

HRID 639537 reaction equation
[CH:1]([N:4]=[C:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[CH2:8]([O:10][C:11](=[O:22])[C:12](=[CH:18]OCC)[C:13](OCC)=[O:14])[CH3:9]>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH:5]([N:4]1[C:1]([CH3:3])=[CH:2][CH:18]=[C:12]([C:11]([O:10][CH2:8][CH3:9])=[O:22])[C:13]1=[O:14])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 1378922-Propanamine, N-(1-methylethylidene)-

Product 1

HCID 59255053HCID 59255053, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Conditions

Temperature
185 °C

Procedure

A mixture of isopropyl(1-methylethylidene)amine (7.94 g, 80.0 mmol, prepared according to Newcomb, Martin et al., J. Amer. Chem. Soc., 1990, 112, 5186) and diethyl(ethoxymethylene)malonate (17.31 g, 80.0 mmol) in diphenyl ether (48 mL) was stirred in a sealed tube at 180-190° C. for 18 h. After cooling, the mixture was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (v/v=1/1˜1/2) to give 12.5 g (70%) of the title compound as brown oil.

Workup

  1. temperatureAfter cooling
  2. customthe mixture was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (v/v=1/1˜1/2)

Sources & evidence

ORD record
ord-fff9c7399a8a4d669d53c55ae152a755
Source dataset
uspto-grants-2010_04
Patent number
US07691881B2

Reaction notes

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