Reacción #48663

Ecuación de reacción

tetrahydropyran-4-one

chloroacetonitrile

potassium tert-butoxide

→

desired compound

Rendimiento 59.1%

1,6-Dioxa-spiro[2,5]octane-2-carbonitrile

Rendimiento 59.1%

Disolventes

tert-butanol

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONadd
2. 2
   Otroover 20 minutes
3. 3
   Otroquench slowly with 1 N hydrochloric acid
4. 4
   ExtracciónExtract with diethyl ether (×3)
5. 5
   LavadoCombine extracts and wash with saturated aqueous sodium chloride solution
6. 6
   Secadodry (magnesium sulfate)
7. 7
   Filtraciónfilter
8. 8
   Concentraciónconcentrate
9. 9
   Otropurify
10. 10
    Lavado(silica gel chromatography, eluting with 0:100 to 1:1 ethyl acetate:hexanes)

Procedimiento

Dissolve tetrahydropyran-4-one (5.0 mL, 54.2 mmol) and chloroacetonitrile (3.4 mL, 53.5 mmol) in tert-butanol (1 mL) and add drop-wise a solution of potassium tert-butoxide (54 mL, 54 mmol, 1.0 M in tert-butanol) over 20 minutes. Stir for 16 hours, dilute with water and quench slowly with 1 N hydrochloric acid. Extract with diethyl ether (×3). Combine extracts and wash with saturated aqueous sodium chloride solution, dry (magnesium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 0:100 to 1:1 ethyl acetate:hexanes) to give the desired compound as a light yellow oil (4.4 g, 59%).

Fuente