Reaktion #55064

Reaktionsgleichung

bromo ether (S)-(+)-3-tert. butoxy-2-methyl-1-bromopropane

sodium cyanide

methanol

→

(R)-(+)-4-tert. butoxy-3-methylbutyronitrile

Ausbeute 64.6%

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONA mixture of 23.1 g
2. 2
   Temperaturrefluxed for 17 hours
3. 3
   TemperaturAfter cooling
4. 4
   Extraktionworked up by extraction with CH2Cl2 in the manner of Example 1
5. 5
   SonstigeThe crude product was chromatographed on 500 g
6. 6
   WaschenElution with 9:1 parts by volume and 4:1 parts by volume hexane-ether
7. 7
   workup.DISTILLATIONfollowed by evaporative distillation

Vorschrift

A mixture of 23.1 g. (0.11 mole) of bromo ether (S)-(+)-3-tert. butoxy-2-methyl-1-bromopropane and 11.07 g. (0.225 mole) of sodium cyanide in 144 ml. of methanol and 36 ml. of water was stirred and refluxed for 17 hours. After cooling, the reaction mixture was diluted with water and worked up by extraction with CH2Cl2 in the manner of Example 1. The crude product was chromatographed on 500 g. of silica gel. Elution with 9:1 parts by volume and 4:1 parts by volume hexane-ether followed by evaporative distillation gave (R)-(+)-4-tert. butoxy-3-methylbutyronitrile (11.03 g.; 64.5%) as a colorless liquid, b.p. 88°-90° C. (bath temperature) (11 mm Hg.); [α]25D+7.41° (c 1.8, C6H6).

Quelle