2-Furanmethanethiol → 3-Chloropropyl-2-furfurylsulfide

HRID 650385Notes

Reaction equation

HRID 650385 reaction equation
C[O-].[Na+].[O:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH2:9][SH:10].Br[CH2:12][CH2:13][CH2:14][Cl:15]>CO.C(#N)C.C(OCC)(=O)C>[Cl:15][CH2:14][CH2:13][CH2:12][S:10][CH2:9][C:5]1[O:4][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 73632-FuranmethanethiolHCID 80061-Bromo-3-chloropropaneHCID 10942334Sodium Methoxide

Product 1

HCID 606423-Chloropropyl-2-furfurylsulfide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.3 ml of a 30% sodium methylate solution in methanol is added in drops to 1.77 ml of furan-2-yl-methanethiol in 18 ml of anhydrous acetonitrile at 0° C. After 5 minutes, the drop-by-drop addition of 2.6 ml of 1-bromo-3-chloropropane is carried out. Then, the reaction solution is allowed to stir for 5 hours at room temperature. For working-up, the batch is diluted with ethyl acetate, washed with water and common salt solution, dried on magnesium sulfate and concentrated by evaporation in a vacuum. Chromatography of the crude product on silica gel with a hexane-ethyl acetate gradient yields 1.1 g of 2-(3-chloropropylthiomethyl)-furan as an oil.

Workup

  1. washwashed with water and common salt solution
  2. customdried on magnesium sulfate
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-1a9ffd0ec0124f8a85ca358fccb716a1
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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