Hydrochloric Acid → (4S)-4-(2-tetrahydropyranyloxy)-1-nonanol

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Reaction Steps

A solution of (4S)-4-(2-tetrahydropyranyloxy)-nonanal (43.5 g., 0.18 mole) in diglyme (125 ml.) is treated with sodium borohydride (3.8 g., 0.10 mole). The temperature rises to 45° with the resulting exothermic reaction. The solution is stirred 4 hours, acidified with concentrated hydrochloric acid, and concentrated on the rotary evaporator. Water is added to the residue and the oily product is taken up in ether; washed with water and brine and dried over sodium sulfate. Evaporation of the ether leaves (4S)-4-(2-tetrahydropyranyloxy)-1-nonanol as a colorless oil to be used in the next step without further purification.

Provenance & Evidence