反应详情

温度

0 °C

To a solution of 3-(1-cyano-1-methylethyl)benzoic acid (8.60 g, 45.5 mmol) produced in Example C6(ii) in toluene (60 mL)/tetrahydrofuran (40 mL) was added dropwise a 1.0M solution (100 mL, 100 mmol) of diisobutylaluminum hydride in hexane at −78° C. for 1 hr. After the completion of the dropwise addition, the mixture was stirred at −78° C. for 1 hr and at 0° C. for 1 hr. The reaction mixture was poured into a mixture of ethyl acetate (200 mL) and 3N hydrochloric acid (300 mL), the organic layer and the aqueous layer were separated, and the aqueous layer was extracted with ethyl acetate (2×100 ml). The combined organic layer was washed with saturated brine (50 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate and hexane to give the title compound (6.39 g, 73%) as colorless crystals.

1. additionAfter the completion of the dropwise addition
2. customthe organic layer and the aqueous layer were separated
3. extractionthe aqueous layer was extracted with ethyl acetate (2×100 ml)
4. washThe combined organic layer was washed with saturated brine (50 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationThe insoluble material was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe obtained residue was recrystallized from ethyl acetate and hexane