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

HRID 1776278Notes

Reaction equation

HRID 1776278 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-c8dcf434ff3e457687d8c40446f49abc
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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