Dimethylformamide dimethyl acetal → 3-Dimethylamino-2-(furan-2-carbonyl)-acrylic acid ethyl ester

HRID 1355824Notes

Reaction equation

HRID 1355824 reaction equation
[O:1]=[C:2]([C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>>[CH2:7]([O:6][C:4](=[O:5])[C:3]([C:2]([C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)=[O:1])=[CH:16][N:17]([CH3:19])[CH3:18])[CH3:8]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 2759240Ethyl 3-(fur-2-yl)-3-oxopropanoate

Product 1

HCID 700025503-Dimethylamino-2-(furan-2-carbonyl)-acrylic acid ethyl esterYield 52.1%

Procedure

Following the method of Menozzi et al. (J. Heterocyclic Chem. 1987, 24, 1669), a mixture of 5.3 g (29.1 mmol) ethyl beta-oxo-2-furanpropionate and 7.7 ml (57.8 mmol) N,N-dimethylformamide dimethyl acetal was stirred for 6.5 hours at room temperature. The reaction mixture was then concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic phase was dried with sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate) afforded 3.6 g (52%) 3-dimethylamino-2-(furan-2-carbonyl)-acrylic acid ethyl ester as a yellow oil. EI-MS m/e (%): 237 (M+, 36), 163 ([M—EtOH—CO]+, 100), 95 (86).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried with sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce196bbcee874937bf2ea2dba252d7b7
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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