反应详情

A mixture of 5-methoxy-3-propyl-1-indanone (184 mg, 0.90 mmol) and (2-ethyl-[1,3]dioxolan-2-yl)acetaldehyde (173 mg, 1.20 mmol) was treated with a solution of KOH (85% wt. pure, 20 mg, 0.30 mmol) in ethanol (1.0 mL). The resulting mixture was stirred at room temperature for 30 minutes, then treated with 10% Pd on carbon (9 mg), placed under a hydrogen atmosphere, and stirred vigorously at room temperature for 18 hours. The mixture was acidified with 2N HCl and partitioned between EtOAc (9 mL) and water (5 mL). The organic phase was washed with brine, dried over MgSO4, filtered, and evaporated under vacuum to an oil (316 mg). The crude product was purified by chromatography on a Biotage FLASH 12M column, eluting with 10% EtOAc in hexanes, to afford 2-[2-(2-ethyl-[1,3]dioxolan-2-yl)-ethyl]-5-methoxy-3-propyl-1-indanone (87 mg) as an oil.

1. stirringstirred vigorously at room temperature for 18 hours
2. custompartitioned between EtOAc (9 mL) and water (5 mL)
3. washThe organic phase was washed with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated under vacuum to an oil (316 mg)
7. customThe crude product was purified by chromatography on a Biotage FLASH 12M column
8. washeluting with 10% EtOAc in hexanes