Diethyl (ethoxymethylene)malonate → HCID 59255053, compound

HRID 1809348Notes

Reaction equation

HRID 1809348 reaction equation
[CH:1]([N:4]=[C:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].C([O:10][CH:11]=[C:12]([C:18](OCC)=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])C>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:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]1=[O:10])([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-0148654cfe5b4088a5486aacd9a0647f
Source dataset
uspto-grants-2013_01
Patent number
US08362038B2

Reaction notes

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