Réaction #48663

Équation de réaction

tetrahydropyran-4-one

chloroacetonitrile

potassium tert-butoxide

→

desired compound

Rendement 59.1%

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

Rendement 59.1%

Solvants

tert-butanol

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONadd
2. 2
   Autreover 20 minutes
3. 3
   Autrequench slowly with 1 N hydrochloric acid
4. 4
   ExtractionExtract with diethyl ether (×3)
5. 5
   LavageCombine extracts and wash with saturated aqueous sodium chloride solution
6. 6
   Séchagedry (magnesium sulfate)
7. 7
   Filtrationfilter
8. 8
   Concentrationconcentrate
9. 9
   Autrepurify
10. 10
    Lavage(silica gel chromatography, eluting with 0:100 to 1:1 ethyl acetate:hexanes)

Mode opératoire

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%).

Source