Water → 3-[(2,5-Dimethylfuran-3-yl)sulfanyl]heptan-4-one

HRID 1287940Notes

Reaction equation

HRID 1287940 reaction equation
C[O-].[Na+].[CH3:4][C:5]1[O:6][C:7]([CH3:11])=[CH:8][C:9]=1[SH:10].Cl[CH:13]([C:16](=[O:20])[CH2:17][CH2:18][CH3:19])[CH2:14][CH3:15].O>CO>[CH2:14]([CH:13]([S:10][C:9]1[CH:8]=[C:7]([CH3:11])[O:6][C:5]=1[CH3:4])[C:16]([CH2:17][CH2:18][CH3:19])=[O:20])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 415692,5-Dimethyl-3-furanthiolHCID 1085444-Heptanone, 3-chloro-HCID 10942334Sodium Methoxide3×

Product 1

HCID 536782963-[(2,5-Dimethylfuran-3-yl)sulfanyl]heptan-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
23 °C

Procedure

Into a 25 ml round bottom 3 neck flask equipped with magnetic stirrer, Y tube, nitrogen inlet, reflux condenser and thermometer is placed a solution of 0.27 g (0.005 moles) of sodium methoxide dissolved in 3 ml absolute methanol. The sodium methoxide solution is cooled using a water bath to 25° C. A solution of 0.64 g (0.005 moles) of 2,5-dimethyl-3-furan thiol in 3 ml of absolute methanol is then added to the sodium methoxide solution dropwise from a pipette while maintaining the temperature of the reaction mass between 22° C and 28° C. While maintaining the temperature of the reaction mass at 23° - 35° C, 3-chloro-4-heptanone (0.74 g; 0.005 moles) in 1 ml absolute methanol is added dropwise. The reaction mass is then stirred for a period of 1 hour while maintaining the temperature at 23° C. After this 1 hour period, 15 ml of water is added with stirring and the reaction mass temperature rises to 28° - 30° C. The reaction mass is cooled to 25° C using a water bath and now exists in an aqueous phase and an organic phase. The aqueous phase (pH=6) is extracted with two 6 ml portions of n-hexane; and the hexane extracts and organic phase are combined, washed with a 4 ml portion of saturated sodium chloride solution and then dried over anhydrous sodium sulfate. The resulting material is gravity filtered and concentrated on a rotary evaporator at 25° - 35° C and 15 mm Hg pressure, yielding a crude yellow oil weighing 1.2 g. The desired product is isolated by GLC trapping (8 foot × 1/4 inch SE-30 Column), and NMR, IR and Mass Spectral analyses yield the information that this material has the structure: ##SPC16##

Workup

  1. customInto a 25 ml round bottom 3 neck flask equipped with magnetic stirrer
  2. temperatureY tube, nitrogen inlet, reflux condenser
  3. customto 25° C
  4. temperaturewhile maintaining the temperature of the reaction mass between 22° C and 28° C
  5. temperatureWhile maintaining the temperature of the reaction mass at 23° - 35° C
  6. stirringwith stirring
  7. customrises to 28° - 30° C
  8. temperatureThe reaction mass is cooled to 25° C
  9. extractionThe aqueous phase (pH=6) is extracted with two 6 ml portions of n-hexane
  10. washwashed with a 4 ml portion of saturated sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated on a rotary evaporator at 25° - 35° C
  14. custom15 mm Hg pressure, yielding a crude yellow oil

Sources & evidence

ORD record
ord-628a39ab4ed54e7787a8c37cff786099
Source dataset
uspto-grants-1976_10
Patent number
US03985907

Reaction notes

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