Reaktion #353412

Reaktionsgleichung

NaH

2-benzyloxymethyl-1,3-propanediol

t-Butyldimethylsilylchloride

→

2-benzyloxymethyl-3-t-butyldimethylsiloxy-1-propanol

Ausbeute 82.0%

Lösungsmittel

ethyl acetate

pentane

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedried in vacuo
2. 2
   Sonstigeto give a white slurry
3. 3
   workup.STIRRINGthe reaction mixture stirred at room temperature for 2 hours further
4. 4
   Waschenwashed with 10% aqueous potassium carbonate and brine
5. 5
   Trocknendried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   Sonstigeto give a colorless oil
9. 9
   SonstigePurification by column chromatography on silica gel (ethyl acetate/hexanes)

Vorschrift

NaH (0.87 g, 80% dispersion in oil, 29.1 mmol) was washed three times with dry pentane, dried in vacuo, and then suspended in 60 mL of dry THF. A solution of 2-benzyloxymethyl-1,3-propanediol (5.70 g, 29.1 mmol) in 5 mL of THF was next added dropwise over 20 min. and the reaction mixture stirred at room temperature for 1.5 hrs. to give a white slurry. t-Butyldimethylsilylchloride (4.38 g, 29.1 mmol) was then added portionwise over 3 min. and the reaction mixture stirred at room temperature for 2 hours further. The mixture was next diluted with 150 mL of ethyl acetate and washed with 10% aqueous potassium carbonate and brine, dried over MgSO4, filtered, and concentrated to give a colorless oil. Purification by column chromatography on silica gel (ethyl acetate/hexanes) provided 7.41 g (82%) of 2-benzyloxymethyl-3-t-butyldimethylsiloxy-1-propanol as a clear, colorless liquid.

Quelle