2-Furanmethanethiol → 4-Furfurylthio-2-pentanone

HRID 1859264

Reaction equation

HRID 1859264 reaction equation
[CH2:1]([SH:7])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9](=[O:13])[CH:10]=[CH:11][CH3:12]>C(O)C>[O:6]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:1][S:7][CH:11]([CH3:12])[CH2:10][C:9](=[O:13])[CH3:8]

Participants

4

Reactant 2

HCID 73632-FuranmethanethiolHCID 12248Pentenone

Product 1

HCID 30259394-Furfurylthio-2-pentanoneYield 51.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g of furfurylmercaptan and 15 g of 3-penten-2-one were dissolved in 100 ml of ethanol. The solution was stirred at room temperature for 48 hours. The solvent was then distilled off in vacuo at 50° C. The residue (18 g) was purified by preparative high pressure liquid chromatography (HPLC). 9 g of 4-[(furylmethyl)thio]-2-pentanone (purity 95%) were obtained. The IR, NMR and mass spectra of the compound agree with the structure described for it.

Workup

  1. distillationThe solvent was then distilled off in vacuo at 50° C
  2. customThe residue (18 g) was purified by preparative high pressure liquid chromatography (HPLC)

Sources & evidence

ORD record
ord-d0b47cf1bf99457397c9e061e28d2c95
Source dataset
uspto-grants-2000_11
Patent number
US06153770

Linked notes

Loading…