反応 #8173

反応方程式

mCPBA

11D

Bicyclo[2.2.2]oct-2-ene-2-carboxylic acid (4-nitro-3-trifluoromethylphenyl)-amide

→

compound 11E

収率 58.0%

3-Oxa-tricyclo[3.2.2.02,4]nonane-2-carboxylic acid (4-nitro-3-trifluoromethyl-phenyl)-amide

収率 58.0%

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   洗浄The organic solution was washed with sat. NaHCO3 (1×50 mL), brine (1×50 mL)
2. 2
   乾燥dried over Na2SO4
3. 3
   濃縮concentrated under reduced pressure
4. 4
   その他Purification by flash chromatography on silica gel eluting with 80% CH2Cl2/hexane

実験手順

mCPBA (60% mixture, 518 mg, 3.00 mmol, 3 eq) was added to a solution of 11D (340 mg, 1.0 mmol, 1.0 eq) in CH2Cl2 (20 mL). The reaction mixture was stirred at rt overnight and then diluted with CH2Cl2 (40 mL). The organic solution was washed with sat. NaHCO3 (1×50 mL), brine (1×50 mL), dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with 80% CH2Cl2/hexane gave 205 mg (0.58 mmol, 57.6%) of compound 11E. HPLC conditions: 95% at 3.70 min (YMC S5 ODS 4.6×50 mm, 10%-90% aqueous methanol over 4 minute gradient with 0.2% H3PO4, detecting at 220 nm). F. 3-Oxa-tricyclo[3.2.2.02,4]nonane-2-carboxylic acid N-(4-nitro-3-trifluoromethyl-phenyl)-hydrazide (11F)

出典