Propyl mercaptan → HCID 53687591, compound

HRID 430754Notes

Reaction equation

HRID 430754 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH3:14])[C:7]=2[O:6][C:5]=1[CH2:15][CH:16]=[CH2:17].C(S)CC.CC(C)([O-])C.[K+].BrC[C:30]([O:32][CH3:33])=[O:31]>CN(C=O)C.O>[OH:1][CH2:2][CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]([O:13][CH2:14][C:30]([O:32][CH3:33])=[O:31])[C:7]=2[O:6][C:5]=1[CH:15]=[CH:16][CH3:17]

Participants

7

Reactant 4

HCID 7848Propyl mercaptanHCID 60984Methyl bromoacetateHCID 11470296HCID 11470296, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 53687591HCID 53687591, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(2-hydroxyethyl)-7-methoxy-2-(2-propenyl)benzofuran (1.43 g), n-propanethiol (0.84 ml) and potassium t-butoxide (968 mg) were dissolved in DMF (15 ml) and the solution was stirred at room temperature for 5 minutes and then at 100° C. for 5 hours. After cooling the reaction temperature to room temperature, methyl bromoacetate (0.87 ml) was added and the solution was stirred at room temperature for 2 hours. The reaction solution was poured into water (150 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated aqueous sodium hydrogen carbonate solution and with saturated brine, followed by drying the resultant over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1) using silica gel to obtain the desired compound (630 mg, yield: 35%).

Workup

  1. waitat 100° C. for 5 hours
  2. temperatureAfter cooling the reaction temperature to room temperature
  3. stirringthe solution was stirred at room temperature for 2 hours
  4. extractionthe resultant was extracted twice with ethyl acetate (20 ml)
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution and with saturated brine
  6. dry with materialby drying the resultant over sodium sulfate
  7. customAfter removing the sodium sulfate
  8. filtrationby filtration
  9. customthe solvent was removed under reduced pressure
  10. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-291c78519f3049139cf21a88446bfe2a
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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