Reaktion #46216

Reaktionsgleichung

6-chloromethyl-2,3-dihydro-benzo[1,4]dioxine

NaCN

water

→

2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acetonitrile

Ausbeute 86.0%

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with dichloromethane (50 mL×4)
2. 2
   WaschenThe combined organic layers were washed with water (50 mL×2) and brine (50 mL)
3. 3
   Trocknendried over Na2SO4
4. 4
   Einengenconcentrated to dryness
5. 5
   SonstigeThe residue was purified by column (Petroleum Ether/Ethyl Acetate 50:1) on silica gel

Vorschrift

A mixture of 6-chloromethyl-2,3-dihydro-benzo[1,4]dioxine (12.5 g, 67.7 mmol) and NaCN (4.30 g, 87.8 mmol) in DMSO (50 mL) was stirred at rt for 1 h. The mixture was poured into water (150 mL) and then extracted with dichloromethane (50 mL×4). The combined organic layers were washed with water (50 mL×2) and brine (50 mL), dried over Na2SO4 and concentrated to dryness. The residue was purified by column (Petroleum Ether/Ethyl Acetate 50:1) on silica gel to obtain 2-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)acetonitrile as a yellow oil (10.2 g, 86%). 1H-NMR (300 MHz, CDCl3) δ 6.78-6.86 (m, 3H), 4.25 (s, 4H), 3.63 (s, 2H).

Quelle