Réaction #2254203

Équation de réaction

H2O

KOH

methyl 2-cyano-2-[4-(4-fluorophenyl)oxan-4-yl]acetate

→

2-[4-(4-fluorophenyl)oxan-4-yl]acetonitrile

Solvants

ethylene glycol

Conditions de réaction

Traitement

1. 1
   Températurecooled
2. 2
   Extractionthe product extracted with Et2O (3×50 ml)
3. 3
   Lavagewashed with H2O (50 ml)
4. 4
   Autredried over NA2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutrePurified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes)

Mode opératoire

To a pre-dissolved solution of KOH (441 mg, 7.87 mmol) in ethylene glycol (20 ml) was added methyl 2-cyano-2-[4-(4-fluorophenyl)oxan-4-yl]acetate (1.09 g, 3.93 mmol). The mixture was heated to 120° C. for 3 h, and then cooled. H2O was added (50 ml), the product extracted with Et2O (3×50 ml), washed with H2O (50 ml), dried over NA2SO4, filtered and concentrated. Purified by normal phase SiO2 chromatography (5 to 40% EtOAc/hexanes) to give 2-[4-(4-fluorophenyl)oxan-4-yl]acetonitrile as a colorless oil (450 mg, 78%, m/z: 219.1 [M+H]+ observed).

Source