反应详情

A solution of 2-allyl-2-butyl-6-methoxy-3,4-dihydro-1(2H)-naphthalenone (931 mg, 3.4 mmol) in acetonitrile (10 mL) was treated with benzoquinone (553 mg, 5.12 mmol), palladium(II) acetate (155 mg, 0.69 mmol), water (0.50 mL, 28 mmol), and perchloric acid (70%, ˜0.14 mL, 1.6 mmol). The resulting mixture was stirred overnight at room temperature. The mixture was partitioned between CH2Cl2 (200 mL) and water (100 mL) and the aqueous phase was back-extracted with CH2Cl2 (2×75 mL). The combined organics were washed with brine, dried over MgSO4, filtered, and concentrated under vacuum. The residue (1.17 g) was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4×7 cm) silica gel column, eluting with 10:1 to 5:1 hexane-EtOAc. The product-containing fractions were evaporated under vacuum to afford 2-butyl-6-methoxy-2-(2-oxopropyl)-3,4-dihydro-1(2H)-naphthalenone as an oil.

1. customThe mixture was partitioned between CH2Cl2 (200 mL) and water (100 mL)
2. extractionthe aqueous phase was back-extracted with CH2Cl2 (2×75 mL)
3. washThe combined organics were washed with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under vacuum
7. customThe residue (1.17 g) was purified by Biotage™ (Charlottesville, Va.) flash chromatography on a 40S (4×7 cm) silica gel column
8. washeluting with 10:1 to 5:1 hexane-EtOAc
9. customThe product-containing fractions were evaporated under vacuum