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With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; dichloromethane; at 20℃;
The crude compound obtained in the second step (85.3 g) and triphenylphosphine (133.8 g) were dissolved in methylene chloride (400 ml). To this solution, a solution of carbon tetrabromide (169.1 g) in THF (300 ml) was slowly added dropwise at room temperature, and the mixture was stirred at room temperature for another 3 hours. Saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate were added to the reaction mixture obtained, and mixed. Then, the mixture was allowed to stand until it had separated into an organic phase and an aqueous phase, and an extractive operation to an organic phase was carried. The organic phase obtained was sequentially washed with water, saturated brine, and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure giving the residue. The residue was a light yellow solid. The residue obtained was purified with a fractional operation by means of column chromatography using n-heptane as the eluent and silica gel as the stationary phase powder, and dried, giving 82.3 g of trans-4'-bromomethyl-trans-4-pentyl-bicyclohexyl (4). The compound (4) obtained was a colorless solid. The yield based on the compound (2) was 73.6%.
Lithiumaluminumhydride (6.4 g) was suspended in THF (500 ml). The compound (2) (100.0 g) was added dropwise in the temperature range of 3 C to 10 C to this suspension, and the mixture was stirred for another 2 hours in this temperature range. After completion of the reaction had been confirmed by means of gas chromatographic analysis, ethyl acetate and a saturated aqueous ammonia solution were sequentially added to the reaction mixture on an ice bath, and the deposit was removed by filtration through celite. The filtrate was extracted with ethyl acetate. The organic phase obtained was sequentially washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solution was concentrated under reduced pressure, giving 85.3 g of a crude compound containing (trans-4'-pentylbicyclohexyl-trans-4-yl) methanol (3). The crude compound obtained was a colorless solid.