反応 #162296

反応方程式

azepan-2-one

trimethyloxonium tetrafluoroborate

→

(E)-7-methoxy-3,4,5,6-tetrahydro-2H-azepine

収率 95.0%

溶媒

DCM

反応条件

後処理

1. 1
   その他The reaction was quenched by the addition of saturated aqueous NaHCO3 (5 ml) (caution: vigorous CO2 evolution)
2. 2
   workup.ADDITIONMore aqueous sodium hydrogen carbonate was added until the aqueous layer
3. 3
   その他The organic layer was removed
4. 4
   抽出the aqueous layer extracted with DCM (5 mL)
5. 5
   乾燥Combined organic layers were dried over anhydrous sodium sulfate
6. 6
   ろ過filtered
7. 7
   その他evaporated under reduced pressure

実験手順

To a solution of azepan-2-one (1.13 g, 10.0 mmol) in DCM (10 mL) in a 40 mL screw cap vial was added freshly prepared trimethyloxonium tetrafluoroborate (1.57 g, 10.59 mmol). The resulting suspension was shaken overnight. The reaction was quenched by the addition of saturated aqueous NaHCO3 (5 ml) (caution: vigorous CO2 evolution). More aqueous sodium hydrogen carbonate was added until the aqueous layer reached pH 8. The organic layer was removed and the aqueous layer extracted with DCM (5 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield (E)-7-methoxy-3,4,5,6-tetrahydro-2H-azepine (1.2 g, 95%) as a clear oil. LCMS (+ESI) m/z 128.2 [M+H]+. 1H-NMR (CDCl3) δ 3.60 (s, 3H), 3.45 (m, 2H), 2.40 (m, 2H), 1.80 (m, 2H), 1.60-1.50 (m, 4H).

出典