반응 #162296

반응 방정식

azepan-2-one

trimethyloxonium tetrafluoroborate

→

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

수율 95.0%

용매

DCM

반응 조건

후처리

1. 1
   기타The 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
   기타The organic layer was removed
4. 4
   추출the aqueous layer extracted with DCM (5 mL)
5. 5
   건조Combined organic layers were dried over anhydrous sodium sulfate
6. 6
   여과filtered
7. 7
   기타evaporated under reduced pressure

실험 절차

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).

출처