Benzyl mercaptan → 4-Benzylthio-2-oxo-2H-pyran

HRID 1084468Notes

Reaction equation

HRID 1084468 reaction equation
Cl[C:2]1[CH:7]=[CH:6][O:5][C:4](=[O:8])[CH:3]=1.[CH2:9]([SH:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH2:9]([S:16][C:2]1[CH:7]=[CH:6][O:5][C:4](=[O:8])[CH:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 11430Potassium Carbonate2×HCID 109314664-Chloro-2H-pyran-2-one

Product 1

HCID 146427864-Benzylthio-2-oxo-2H-pyran

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.433 g (0.0033 mol) of 4-chloro-2-oxo-2H-pyran and 0.41 g (0.0033 mol) of benzyl mercaptan in 2 ml of dimethyl formamide is added 0.228 g (0.00165 mol) of K2CO3. The reaction mixture is stirred for 1 hour and then the same amount of K2CO3 is once more added. The reaction mixture is then stirred overnight at 25° C., diluted with 30 ml of CH2C2, and extracted with 5×50 ml of a saturated aqueous solution of NaCl. The organic phase is dried over Na2SO4 and concentrated in a water jet vacuum. The distillation residue is chromatographed over silica gel. Yield: 0.36 g (50%). Melting point: 105°-106° C.

Workup

  1. stirringThe reaction mixture is then stirred overnight at 25° C.
  2. additiondiluted with 30 ml of CH2C2
  3. extractionextracted with 5×50 ml of a saturated aqueous solution of NaCl
  4. dry with materialThe organic phase is dried over Na2SO4
  5. concentrationconcentrated in a water jet vacuum
  6. distillationThe distillation residue is chromatographed over silica gel

Sources & evidence

ORD record
ord-ab2476385434488d8a6295f604194198
Source dataset
uspto-grants-1991_04
Patent number
US05004814

Reaction notes

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