Dimethylformamide → 6-[(Dimethylamino)methylene]-2-ethoxycyclohex-2-en-1-one

HRID 875120Notes

Reaction equation

HRID 875120 reaction equation
[CH2:1]([O:3][C:4]1[C:5](=[O:10])[CH2:6][CH2:7][CH2:8][CH:9]=1)[CH3:2].[CH3:11][N:12]([CH3:15])[CH:13]=O>>[CH3:11][N:12]([CH:15]=[C:6]1[C:5](=[O:10])[C:4]([O:3][CH2:1][CH3:2])=[CH:9][CH2:8][CH2:7]1)[CH3:13]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 1215982-Ethoxycyclohex-2-en-1-one

Product 1

HCID 666828496-[(Dimethylamino)methylene]-2-ethoxycyclohex-2-en-1-oneYield 80%

Conditions

Temperature
60 °C

Procedure

3.4 g (0.02 mmol) of 2-ethoxycyclohex-2-en-1-one were dissolved in 30 mL of dry dimethylformamide and 30 mL (0.05 mmol) of dimethylformamide dimethyl acetale were added. The solution was stirred at 60° C. for 2 hours. The solvent was then evaporated under vacuum, the residue triturated with diethyl ether and collected by filtration to give 6.6 g of the title compound (80% yield).

Workup

  1. customThe solvent was then evaporated under vacuum
  2. customthe residue triturated with diethyl ether
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-5a0038b9d0574280a7868344cfaf033a
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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