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

Participants

Reaction Conditions

Reaction Steps

(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.

Provenance & Evidence