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

HRID 655460Notes

Reaction equation

HRID 655460 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[O:17])[C:11]#[C:12][C:13](O)([CH3:15])[CH3:14])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C(NCC)C.C([OH:25])C>>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[O:17][C:13]([CH3:14])([CH3:15])[C:12](=[O:25])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 8021DiethylamineHCID 593547741-(3-Chloro-4-methoxyphenyl)-4-hydroxy-4-methylpent-2-yn-1-one

Product 1

HCID 593548485-(3-chloro-4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-oneYield 100%

Procedure

To a stirred solution of 1-(3-chloro-4-methoxyphenyl)-4-hydroxy-4-methylpent-2-yn-1-one (0.7 g, 2.75 mmol) in ethanol (5 mL), a solution of diethyl amine (0.20 g, 2.75 mmol) in EtOH (7 mL) was added dropwise at RT. The reaction mixture was then stirred for additional 30 min. The ethanol was removed, and the reaction mixture diluted with EtOAc (10 mL). The combined organic layers were then washed with water (5 mL) and brine (5 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford 5-(3-chloro-4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (0.7 g, 100%) as a semi solid.

Workup

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

Sources & evidence

ORD record
ord-95620ccfaa3a45dca29a9e35245aec38
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

Loading…