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

HRID 1258334Notes

Reaction equation

HRID 1258334 reaction equation
O[C:2]([CH3:18])([CH3:17])[C:3]#[C:4][C:5]([C:7]1[CH:8]=[CH:9][C:10]([O:15][CH3:16])=[C:11]([CH:14]=1)[C:12]#[N:13])=[O:6].C(NCC)C.C([OH:26])C>>[CH3:17][C:2]1([CH3:18])[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([O:15][CH3:16])=[C:11]([CH:14]=2)[C:12]#[N:13])=[CH:4][C:3]1=[O:26]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 8021DiethylamineHCID 59354801HCID 59354801, compound

Product 1

HCID 670251415-(5,5-Dimethyl-4-oxo-4,5-dihydrofuran-2-yl)-2-methoxybenzonitrileYield 100%

Procedure

To a stirred solution of 5-(4-hydroxy-4-methylpent-2-ynoyl)-2-methoxybenzonitrile (0.9 g, 3.70 mmol) in ethanol (10 mL), a solution of diethyl amine (0.38 mL, 3.70 mmol) in EtOH (2.0 mL) was added dropwise at RT and the reaction mixture was stirred for additional 1 h. The ethanol was then was removed, and the mixture diluted with EtOAc (40 mL). The combined organic layers were washed with water (5 mL) and brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford 5-(5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)-2-methoxybenzonitrile (0.9 g, 100%) as a yellow semi solid.

Workup

  1. customThe ethanol was then was removed
  2. additionthe mixture diluted with EtOAc (40 mL)
  3. washThe combined organic layers were washed with water (5 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a177a2327444474eb7e8eb786951d2de
Source dataset
uspto-grants-2013_06
Patent number
US08466148B2

Reaction notes

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