Dimethylformamide dimethyl acetal → HCID 67513835, compound

HRID 2278410Notes

Reaction equation

HRID 2278410 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:14]=[CH:13][N:12]=[CH:11][CH:10]=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:14]=[CH:13][N:12]=[CH:11][CH:10]=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 65582892HCID 65582892, compound

Product 1

HCID 67513835HCID 67513835, compoundYield 86%

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(2-methyl-3-furanyl)-2-(4-pyridinyl)ethanone (1.006 g, 5 mmol) in N,N-dimethylformamide dimethyl acetal (0.664 ml, 5 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 oil (1.1 g, 86%). 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-82c299a4d35a40b8a3f1a4a8a5b63b19
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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