Dimethylformamide dimethyl acetal → HCID 67514434, compound

HRID 2278416Notes

Reaction equation

HRID 2278416 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][CH:12]=[CH:11][N: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][CH:12]=[CH:11][N: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 43118496HCID 43118496, compound

Product 1

HCID 67514434HCID 67514434, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(2-methyl-3-furanyl)-2-(2-pyridinyl)ethanone (1.207 g, 6 mmol) in N,N-dimethylformamide dimethyl acetal (0.797 ml, 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 product as a dark orange oil which was used in the next step (1.1 g, 72%). 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-99131bd79eda48e0aefc249dd8d35385
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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