Water → HCID 19373328, compound

HRID 129284Notes

Reaction equation

HRID 129284 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CS(O[CH2:16][C:17]1([CH2:21][CH2:22][CH3:23])[CH2:20][O:19][CH2:18]1)(=O)=O.O>CN(C)C=O>[CH2:1]([S:8][CH2:20][C:17]([CH2:16][S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH2:21][CH2:22][CH3:23])[CH2:18][OH:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7509Benzyl mercaptanHCID 24758Sodium hydrideHCID 193734233-n-Propyloxetan-3-ylmethyl methanesulphonate

Product 1

HCID 19373328HCID 19373328, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of benzyl mercaptan (25.0 ml) in dry dimethylformamide (100 ml) was stirred at 0° C., under a current of nitrogen. Sodium hydride (6.0 g., 80% dispersion in oil) was added carefully and the mixture was stirred at 0° for 1 hour. 3-n-Propyloxetan-3-ylmethyl methanesulphonate (10.0 g.) was added and the mixture was stirred at 0° C. for 1 hour. The mixture was refluxed with stirring for 6 hours. The mixture was cooled and poured into water. The aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with water, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was chromatographed on silica, eluting with 1:4; diethyl ether: hexane. 2,2-Di-(benzylthiomethyl)pentan-1-ol was obtained as a pale yellow oil (15.6 g.)

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 hour
  2. temperatureThe mixture was refluxed
  3. stirringwith stirring for 6 hours
  4. temperatureThe mixture was cooled
  5. extractionThe aqueous mixture was extracted with diethyl ether
  6. washThe ethereal extracts were washed with water
  7. dry with materialdried over anhydrous magnesium sulphate
  8. customevaporated in vacuo
  9. customThe residue was chromatographed on silica
  10. washeluting with 1:4

Sources & evidence

ORD record
ord-2edfacb127504e38b3dc89f00efc6409
Source dataset
uspto-grants-1995_11
Patent number
US05466710

Reaction notes

Loading…