Ethanol → 5-(4-Methoxyphenyl)-2,2-dimethylfuran-3(2H)-one

HRID 655379Notes

Reaction equation

HRID 655379 reaction equation
O[C:2]([CH3:16])([CH3:15])[C:3]#[C:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:6].CC[OH:19]>>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[O:6][C:2]([CH3:16])([CH3:15])[C:3](=[O:19])[CH:4]=2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 702Ethanol2×HCID 127225774-Hydroxy-1-(4-methoxyphenyl)-4-methylpent-2-yn-1-one

Product 1

HCID 145333195-(4-Methoxyphenyl)-2,2-dimethylfuran-3(2H)-oneYield 92%

Procedure

To a stirred solution of 4-hydroxy-1-(4-methoxyphenyl)-4-methylpent-2-yn-1-one (6 g, 0.027 mol) in ethanol (100 mL) diethyl amine (2.86 g, 0.027 mol) in EtOH (15 mL) was added dropwise at RT and the reaction mixture was stirred for additional 4 h. The EtOH was then removed and the mixture 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 5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (5.5 g, 92%).

Workup

  1. customThe EtOH was then removed
  2. additionthe mixture 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-74bdd62f6da24dc0b0de8c6cb8c050a9
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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