反応 #7930

反応方程式

4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

copper(I) cyanide

→

9a-butyl-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

収率 81.0%

溶媒

1-methyl-2-pyrrolidinone

反応条件

後処理

1. 1
   その他The mixture was partitioned between EtOAc (20 mL) and water (20 ml)
2. 2
   洗浄The organic phase was washed with water (2×20 mL) and brine (10 mL)
3. 3
   乾燥dried over MgSO4
4. 4
   ろ過filtered
5. 5
   その他evaporated under vacuum
6. 6
   その他The residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate

実験手順

A solution of 4-bromo-9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (50 mg, 0.138 mmol) in anhydrous 1-methyl-2-pyrrolidinone (0.276 mL) was treated with copper(I) cyanide (25 mg, 0.275 mmol). The resulting mixture was stirred under a nitrogen atmosphere and heated in an oil bath at 160° C. for 40 minutes. The mixture was partitioned between EtOAc (20 mL) and water (20 ml). The organic phase was washed with water (2×20 mL) and brine (10 mL), dried over MgSO4, filtered, and evaporated under vacuum. The residue was purified by preparative layer chromatography on a 0.1×20×20 cm silica gel GF plate, developing with 5% EtOAc in CH2Cl2, to afford 9a-butyl-4-cyano-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (33 mg) as an oil.

出典