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

HRID 1425885Notes

Reaction equation

HRID 1425885 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 (1.8 g, 9.50 mmol) in ethanol (18 mL) was added diethyl amine (1.04 g, 14.0 mmol) in EtOH (1 mL) dropwise at RT and the reaction mixture was stirred for additional 1 h. The reaction mixture was concentrated, diluted with EtOAc (20 mL), washed with water (10 mL), brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford crude 2,2-dimethyl-5-(pyridin-4-yl) furan-3(2H)-one (1.3 g) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc (20 mL)
  3. washwashed with water (10 mL), brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a685fcc1808b4ab3886398429b69938d
Source dataset
uspto-grants-2015_01
Patent number
US08933074B2

Reaction notes

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