Water → 2,2-Di(benzylthiomethyl)pentan-1-ol

HRID 1197336Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1197336
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 193733282,2-Di(benzylthiomethyl)pentan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-da35aecc0d944e18a517f4a189089dc9
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05116862

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