反应详情

First Step Under a nitrogen atmosphere, 2.4 g of 4-(trans-4-propylcyclohexyl)-2-cyclohexene-1-ol (r-1) was dissolved into 50 mL of THF, 0.52 g of 60% sodium hydride was added under ice-cooling, and the resultant mixture was stirred at room temperature for 1 hour. Thereto, 2.3 g of potassium iodide and 3.2 g of (trans-4-pentylcyclohexyl)bromomethane (r-2) dissolved in 30 mL of THF were added, and the resultant mixture was stirred under heating reflux for 8 hours. The resultant reaction mixture was poured into water, and subjected to extraction with toluene. Combined organic layers were washed with saturated brine, and then dried over anhydrous magnesium sulfate. A solvent was evaporated under reduced pressure, and a residue was purified by silica gel column chromatography (eluate:heptane:toluene=1:1 (in a volume ratio)), and further purified by recrystallization from a mixed solvent of heptane: Solmix A-11 (registered tradename; Japan Alcohol Trading Co., Ltd.)=1:2 (in a volume ratio), and thus 0.15 g of 6-(trans-4-propylcyclohexyl)-3-(trans-4-pentylcyclohexyl)methoxy cyclohexene [compound (1-3-1-18) was obtained.

1. additionwas added under ice-
2. temperaturecooling
3. additionwere added
4. temperatureunder heating
5. temperaturereflux for 8 hours
6. customThe resultant reaction mixture
7. extractionsubjected to extraction with toluene
8. washCombined organic layers were washed with saturated brine
9. dry with materialdried over anhydrous magnesium sulfate
10. customA solvent was evaporated under reduced pressure
11. customa residue was purified by silica gel column chromatography (eluate:heptane
12. customtoluene=1:1 (in a volume ratio)), and further purified by recrystallization from a mixed solvent of heptane