Hydrochloric Acid → 2,4-Dimethyl-2-[(2-methylfuran-3-yl)sulfanyl]pentan-3-one

HRID 1287941Notes

Reaction equation

HRID 1287941 reaction equation
[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[SH:7].C[O-].[Na+].Cl[C:12]([CH3:19])([C:14](=[O:18])[CH:15]([CH3:17])[CH3:16])[CH3:13].Cl>CO.O>[CH3:1][C:2]1[O:3][CH:4]=[CH:5][C:6]=1[S:7][C:12]([CH3:19])([CH3:13])[C:14]([CH:15]([CH3:17])[CH3:16])=[O:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 342862-Methyl-3-furanthiolHCID 10942334Sodium MethoxideHCID 122946913-Pentanone, 2-chloro-2,4-dimethyl-

Product 1

HCID 215070772,4-Dimethyl-2-[(2-methylfuran-3-yl)sulfanyl]pentan-3-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

Into a 25 ml round bottom 3 neck flask equipped with magnetic stirrer, Y tube, nitrogen inlet, reflux condenser, thermometer and heating mantle, is added 0.57 g (0.005 moles) 2-methyl-3-furan thiol in 3 ml absolute methanol and a solution of 0.27 g (0.005 moles) sodium methoxide in 3 ml of absolute methanol. After 10 minutes stirring, 0.74 g (0.005 moles) 2-chloro-2,4-dimethyl-3-pentanone in 1 ml absolute methanol is added slowly. The reaction mass is then warmed to 35° C using a hot water bath and while maintaining the temperature of the reaction mass at 35° C it is placed under a nitrogen blanket. The reaction mass is then heated to reflux (65°-66° C) and refluxed for a period of 1 hour. At the end of the 1 hour reflux period, the reaction mass is allowed to cool and is worked up by adding thereto 10 ml of water. The reaction mass, being at a basic pH (9-10), is acidified with dilute HCl bringing the pH down to 6. N-Hexane is added to the reaction mass giving rise to two phases; an aqueous phase and an organic phase. The aqueous phase is extracted with 2 × 10 ml of hexane. The hexane extracts are separated, combined, washed with saturated sodium chloride solution and then dried over anhydrous sodium sulfate. The resulting solution is then concentrated to a weight of 1.02 g and the desired compound is isolated using GLC apparatus (conditions: SE-30 Column, 8 foot × 1/4 inch). NMR, IR and Mass Spectral analyses confirm that the structure of the resulting material is: ##SPC20##

Workup

  1. customInto a 25 ml round bottom 3 neck flask equipped with magnetic stirrer
  2. temperatureY tube, nitrogen inlet, reflux condenser
  3. temperaturethermometer and heating mantle
  4. temperaturewhile maintaining the temperature of the reaction mass at 35° C it
  5. temperatureThe reaction mass is then heated
  6. temperatureto reflux (65°-66° C)
  7. temperaturerefluxed for a period of 1 hour
  8. temperatureAt the end of the 1 hour reflux period
  9. temperatureto cool
  10. additionby adding
  11. customgiving rise to two phases
  12. extractionThe aqueous phase is extracted with 2 × 10 ml of hexane
  13. customThe hexane extracts are separated
  14. washwashed with saturated sodium chloride solution
  15. dry with materialdried over anhydrous sodium sulfate
  16. concentrationThe resulting solution is then concentrated to a weight of 1.02 g

Sources & evidence

ORD record
ord-9e208a9c43554ca4b6203f8c19620d58
Source dataset
uspto-grants-1976_10
Patent number
US03985907

Reaction notes

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