反応式
Br[C:2]1[C:3](=[O:22])[CH2:4][CH2:5][C:6]2([CH2:18][CH2:19][CH2:20][CH3:21])[C:14]=1[C:13]1[C:8](=[C:9]([Cl:17])[C:10]([O:15][CH3:16])=[CH:11][CH:12]=1)[CH2:7]2.[Cu][C:24]#[N:25]>CN1CCCC1=O>[CH2:18]([C:6]12[CH2:5][CH2:4][C:3](=[O:22])[C:2]([C:24]#[N:25])=[C:14]1[C:13]1[C:8](=[C:9]([Cl:17])[C:10]([O:15][CH3:16])=[CH:11][CH:12]=1)[CH2:7]2)[CH2:19][CH2:20][CH3:21]参加物
反応条件
- 温度
- 150 °C
実験手順
A solution of 4-bromo-9a-butyl-8-chloro-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (103 mg, 0.268 mmol) in anhydrous 1-methyl-2-pyrrolidinone (0.54 mL) was treated with copper(I) cyanide (24 mg, 0.268 mmol). The mixture was placed under a nitrogen atmosphere, stirred, and heated in an oil bath at 150° C. for 1.5 hours. After cooling to room temperature, the mixture was partitioned between EtOAc (50 mL) and water (50 mL). The organic phase was washed with water (5×50 mL) and brine (50 mL), dried over MgSO4, filtered, and evaporated under vacuum to an oil. The crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 5% EtOAc in CH2Cl2. The product band was eluted with EtOAc and the eluent evaporated under vacuum to afford 9a-butyl-8-chloro-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (65 mg) as an oil.
後処理
- temperatureAfter cooling to room temperature
- customthe mixture was partitioned between EtOAc (50 mL) and water (50 mL)
- washThe organic phase was washed with water (5×50 mL) and brine (50 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated under vacuum to an oil
- customThe crude product was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate
- washThe product band was eluted with EtOAc
- customthe eluent evaporated under vacuum
出典と根拠
- ORDレコード
- ord-e993677936f64b12a731aaf297bed3e9
- 出典データセット
- uspto-grants-2006_08
- 特許番号
- US07087599B2
関連ノート
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