反応 #40784

反応方程式

Malononitrile

bis(2-bromoethyl)ether

KOtBu

→

solid

収率 24.0%

Tetrahydro-pyran-4,4-dicarbonitrile

収率 24.0%

溶媒

DCM

DMSO

反応条件

後処理

1. 1
   抽出extracted 3 times with 5% aqueous NaHCO3
2. 2
   乾燥The organic phase was dried over Na2SO4
3. 3
   その他evaporated under reduced pressure
4. 4
   その他The crude material was purified by flash chromatography
5. 5
   洗浄eluting with PA

実験手順

Malononitrile (5.0 g) was dissolved in DMSO (5 mL). Subsequently, bis(2-bromoethyl)ether (9.49 mL) and TBAB (1.22 g) were added, followed by portionwise addition of KOtBu (8.49 g). The mixture was stirred for 4 h. at room temperature, taken up in DCM and extracted 3 times with 5% aqueous NaHCO3. The organic phase was dried over Na2SO4 and evaporated under reduced pressure. The crude material was purified by flash chromatography eluting with PA:Et2O 65:35 (Rf=0.24, visualized with KMnO4) to give 2.49 g (24%) of a solid. 1H NMR (400 MHz, CDCl3) δ 2.24 (t, 4H), 3.87 (t, 4H).

出典