Ethanol → 2-ethyl-2-methyl-5-{4-(methylthio)phenyl}-3(2H)-furanone

HRID 2298288Notes

Reaction equation

HRID 2298288 reaction equation
O[C:2]([CH3:17])([CH2:15][CH3:16])[C:3]#[C:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)=[O:6].C(NCC)C.C([OH:25])C>>[CH2:15]([C:2]1([CH3:17])[C:3](=[O:25])[CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=2)[O:6]1)[CH3:16]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 8021DiethylamineHCID 183861674-Hydroxy-4-methyl-1-{4-(methylthio)phenyl}-2-hexyn-1-one

Product 1

HCID 183860632-ethyl-2-methyl-5-{4-(methylthio)phenyl}-3(2H)-furanone

Procedure

5.34 g of 4-hydroxy-4-methyl-1-{4-(methylthio)phenyl}-2-hexyn-1-one was dissolved in 200 ml ethanol, added dropwise 3 ml diethylamine diluted with 50 ml ethanol. The reaction solution was stirred at room temperature for 4 hours, and the solvent was removed in vacuo. The resulting residue was extracted with water and dichloromethane (100 ml×3). Concentration of the organic layer afforded crude 2-ethyl-2-methyl-5-{4-(methylthio)phenyl}-3(2H)-furanone, which was used in the next step without further purification.

Workup

  1. customthe solvent was removed in vacuo
  2. extractionThe resulting residue was extracted with water and dichloromethane (100 ml×3)

Sources & evidence

ORD record
ord-6b04ba60b7fa4fefb044c941b52e9d06
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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