Ethanol → 4-(5,5-Dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile

HRID 655428Notes

Reaction equation

HRID 655428 reaction equation
O[C:2]([CH3:16])([CH3:15])[C:3]#[C:4][C:5]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)=[O:6].C(NCC)C.C([OH:24])C>>[CH3:15][C:2]1([CH3:16])[O:6][C:5]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)=[CH:4][C:3]1=[O:24]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 8021DiethylamineHCID 666439664-(4-Hydroxy-4-methylpent-2-ynoyl)benzonitrile

Product 1

HCID 595801574-(5,5-Dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile

Procedure

To a stirred solution of crude 4-(4-hydroxy-4-methylpent-2-ynoyl)benzonitrile (1.2 g, 5.60 mmol) in ethanol (12 mL), a solution of diethyl amine (0.58 mL, 5.60 mmol) in EtOH (5 mL) was added dropwise at RT. The reaction mixture was then stirred for additional 1 h. The ethanol was removed and the mixture then diluted with EtOAc (50 mL). The combined organic layers were washed with water (10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford crude 4-(5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)benzonitrile (1.2 g) as a light green semi solid which was taken on to the next step without further purification.

Workup

  1. customThe ethanol was removed
  2. additionthe mixture then diluted with EtOAc (50 mL)
  3. washThe combined organic layers were washed with water (10 mL), brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c40ab028aa0942b99481fb56fbfc67de
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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