Reaktion #6151

Reaktionsgleichung

diisobutylaluminum hydride

t-butyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanoate

ammonium chloride

hydrochloric acid

→

(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanal

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedid not exceed -70° C
2. 2
   workup.WAITThe mixture was then left
3. 3
   Temperaturto warm to room temperature
4. 4
   workup.STIRRINGAfter stirring for 1 hour the organic phase
5. 5
   Sonstigewas dried
6. 6
   Filtrationfiltered
7. 7
   Sonstigeevaporated
8. 8
   SonstigeThe material obtained
9. 9
   Sonstigewas chromatographed on silica gel

Vorschrift

I)a) 9.2 g of t-butyl (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanoate were dissolved in 115 ml of toluene while gassing with argon and with the exclusion of moisture and cooled to -75° C. 26.5 ml of a 1.2M solution of diisobutylaluminum hydride in toluene were then added dropwise in such a manner that the temperature did not exceed -70° C. After stirring at -75° C. for 1 hour there were added dropwise 7.4 ml of saturated aqueous ammonium chloride solution and subsequently 15.5 ml of 1N hydrochloric acid at -70° C. The mixture was then left to warm to room temperature. After stirring for 1 hour the organic phase was dried, filtered and evaporated. The material obtained was chromatographed on silica gel. There was obtained (R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]tetradecanal as a colorless oil.

Quelle