Reaction #48663

Reaction equation

tetrahydropyran-4-one

chloroacetonitrile

potassium tert-butoxide

→

desired compound

Yield 59.1%

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

Yield 59.1%

Solvents

tert-butanol

water

Conditions

Workup

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

Procedure

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