反応 #7988
ord-3bfd2b8db18a4c68b99e3c5c20362e76
反応方程式
反応物
試薬
反応条件
後処理
- 1その他The solvent was evaporated under vacuum
- 2その他to give a residue
- 3workup.STIRRINGstirred
- 4温度while heating in an 80° C. oil bath for 6 hours
- 5温度After cooling
- 6その他the mixture was partitioned between EtOAc (25 mL) and saturated aqueous K2CO3 (25 mL)
- 7洗浄The organic phase was washed with brine (10 mL)
- 8乾燥dried over MgSO4
- 9ろ過filtered
- 10その他evaporated under vacuum to an oil (138 mg)
- 11その他The crude product was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates
- 12洗浄The product bands were eluted with EtOAc
- 13その他the eluent evaporated under vacuum
実験手順
A solution of 2-butyl-6-fluoro-5-methoxy-4-methyl-1-indanone (118 mg, 0.47 mmol) in anhydrous tetrahydrofuran (0.47 mL) was treated with propyl vinyl ketone (0.065 mL, 0.56 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.0143 mL, 0.094 mmol). The mixture was stirred and heated in an oil bath at 50° C. for 6 hours and then at room temperature for 64 hours. The solvent was evaporated under vacuum to give a residue consisting mainly of 2-butyl-6-fluoro-5-methoxy-4-methyl-2-(3-oxohexyl)-1-indanone. This material was dissolved in acetic acid (2 mL), treated with aqueous 6N HCl (1.5 mL), and stirred while heating in an 80° C. oil bath for 6 hours. After cooling, the mixture was partitioned between EtOAc (25 mL) and saturated aqueous K2CO3 (25 mL). The organic phase was washed with brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil (138 mg). The crude product was purified by preparative layer chromatography on two 0.1×20×20 cm silica gel GF plates, developing with CH2Cl2. The product bands were eluted with EtOAc and the eluent evaporated under vacuum to afford 9a-butyl-4-ethyl-6-fluoro-7-methoxy-8-methyl-1,2,9,9a-tetrahydro-3H-fluoren-3-one (93 mg) as an oil.