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

HRID 1425824Notes

Reaction equation

HRID 1425824 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 room temperature, 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), a solution of diethylamine (0.511 g, 0.007 mol) in EtOH (15 mL) was added dropwise and the reaction mixture was stirred for additional 40 min. The ethanol was removed, and the mixture was then diluted with EtOAc (100 mL). The combined 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 ethanol was removed
  2. additionthe mixture was then diluted with EtOAc (100 mL)
  3. washThe combined 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-732ebf91eb824275b4ec579e587d5011
Source dataset
uspto-grants-2015_01
Patent number
US08933074B2

Reaction notes

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