Dimethylformamide dimethyl acetal → HCID 67513385, compound

HRID 2278412Notes

Reaction equation

HRID 2278412 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[C:7](=[O:15])[CH2:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1.CO[CH:18](OC)[N:19]([CH3:21])[CH3:20]>>[CH3:18][N:19]([CH3:21])[CH:20]=[C:8]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[C:7]([C:6]1[CH:5]=[CH:4][O:3][C:2]=1[CH3:1])=[O:15]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67513775HCID 67513775, compound

Product 1

HCID 67513385HCID 67513385, compoundYield 49%

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(2-methyl-3-furanyl)-2-(3-pyridinyl)ethanone (1207 mg, 6 mmol) in N,N-dimethylformamide dimethyl acetal (797 μl, 6.00 mmol) was heated at 100° C. for 2 hours. The mixture was cooled to room temperature and the solvent was evaporated. The residue was partitioned between ethyl acetate and water. The organic phase was separated, washed with water and brine, dried and evaporated to give the title compound as an orange oil (750 mg, 49%). LC/MS [M+H]+=257.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent was evaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customThe organic phase was separated
  5. washwashed with water and brine
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-d3a35484060c413fa51cbb6ae748d4b5
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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