3,4-dihydro-2H-pyran → (2-Tetrahydropyranyl)oxynorbornyl alcohol

Beteiligte Stoffe

Reaktionsschritte

Into a 200 ml flask having four openings and equipped with a thermometer, a tube for introducing nitrogen gas into the flask, and a reflux tube were put 10.0 grams (0.11 mol) of 3,4-dihydro-2H-pyran, 12.8 grams (100 mmol) of norbornane-2,3-diol and 50 ml of dry tetrahydrofuran. Then, they were stirred. Then, five drops of thick sulfuric acid were added. Thereafter, the mixture was allowed to stand at a room temperature for 24 hours. After the mixture was cooled down to room temperature, 3 grams of solid sodium carbonate and 10 grams of anhydrous sodium sulfate were added to the mixture. Then, the mixture was stirred for 2 hours and filtrated. The gathered filtration was disposed with 0.2 grams of hydrogenated calcium. The residue obtained by removing excessive dihydropyran by means of a rotary evaporator under reduced pressure was refined through a silica gel column, in which ethyl acetate/n-hexane was used as an elution solvent, to thereby obtain 4.0 grams of (2-tetrahydropyranyl)oxynorbornyl alcohol. The yield was 19%. The obtained (2-tetrahydropyranyl)oxynorbornyl alcohol was oily.

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