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

HRID 1776323Notes

Reaction equation

HRID 1776323 reaction equation
O[C:2]([CH3:17])([CH3:16])[C:3]#[C:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)=[O:6].C(NCC)C.C([OH:25])C>>[CH3:16][C:2]1([CH3:17])[C:3](=[O:25])[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)[O:6]1

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 8021DiethylamineHCID 593548124-Hydroxy-4-methyl-1-(4-nitrophenyl)pent-2-yn-1-one

Product 1

HCID 593547702,2-dimethyl-5-(4-nitrophenyl)furan-3(2H)-oneYield 92%

Procedure

To a stirred solution of 4-hydroxy-4-methyl-1-(4-nitrophenyl)pent-2-yn-1-one (1.74 g, 7.46 mmol, 1 eq) in ethanol (30 mL), a solution of diethylamine (778 mg, 7.46 mmol, 1 eq) in EtOH (5 mL) was added dropwise at RT. The reaction mixture was then stirred for additional 90 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-(4-nitrophenyl)furan-3(2H)-one (1.6 g, 92%) which was used in the next step without further purification.

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-84af77387d5048138401c15d792d39c6
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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