Ethanol → 2,2-dimethyl-5-(pyridin-4-yl)furan-3(2H)-one

HRID 1258257Notes

Reaction equation

HRID 1258257 reaction equation
O[C:2]([CH3:14])([CH3:13])[C:3]#[C:4][C:5]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)=[O:6].C(NCC)C.C([OH:22])C>>[CH3:13][C:2]1([CH3:14])[C:3](=[O:22])[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)[O:6]1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 8021DiethylamineHCID 593548164-Hydroxy-4-methyl-1-(pyridin-4-yl)pent-2-yn-1-one

Product 1

HCID 593547902,2-dimethyl-5-(pyridin-4-yl)furan-3(2H)-one

Procedure

To a stirred solution of 4-hydroxy-4-methyl-1-(pyridin-4-yl)pent-2-yn-1-one (1.49 g, 0.007 mol) in ethanol (15 mL), diethylamine (0.511 g, 0.007 mol) in EtOH (15 mL) was added dropwise at RT. The mixture was then stirred for additional 40 min. The EtOH was evaporated and the mixture was diluted with EtOAc (100 mL). The organic layers were washed with water (50 mL) and brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford 2,2-dimethyl-5-(pyridin-4-yl)furan-3(2H)-one (1.4 g).

Workup

  1. customThe EtOH was evaporated
  2. additionthe mixture was diluted with EtOAc (100 mL)
  3. washThe organic layers were washed with water (50 mL) and brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f0751c54e5d4d30815b6a77283979b2
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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