Dimethylformamide dimethyl acetal → Methyl 2-cyclopropanecarbonyl-3-dimethylamino-acrylate

HRID 2109227Notes

Reaction equation

HRID 2109227 reaction equation
[CH3:1][O:2][C:3](=[O:10])[CH2:4][C:5]([CH:7]1[CH2:9][CH2:8]1)=[O:6].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:10])[C:4]([C:5]([CH:7]1[CH2:9][CH2:8]1)=[O:6])=[CH:13][N:14]([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 101300163-Cyclopropyl-3-Oxopropionic Acid Methyl Ester

Product 1

HCID 66877441Methyl 2-cyclopropanecarbonyl-3-dimethylamino-acrylateYield 96.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

3-Cyclopropyl-3-oxo-propionic acid methyl ester (1.25 g, 8.79 mmol) was dissovled in 6.25 mL of CHCl3 and 1.17 mL (8.79 mmol) of dimethylformamide dimethyl acetal was added. The mixture was heated to 60° C. in a sealed vessel overnight. The mixuture was then cooled and concentrated to provide 1.67 g of 2-cyclopropanecarbonyl-3-dimethylamino-acrylic acid methyl ester.

Workup

  1. temperatureThe mixuture was then cooled
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-373bbc83d8f84ec8a561951454ce7f6a
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

Loading…