Реакция #48663

Уравнение реакции

tetrahydropyran-4-one

chloroacetonitrile

potassium tert-butoxide

→

desired compound

Выход 59.1%

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

Выход 59.1%

Растворители

tert-butanol

water

Условия реакции

Обработка

1. 1
   workup.ADDITIONadd
2. 2
   Другоеover 20 minutes
3. 3
   Другоеquench slowly with 1 N hydrochloric acid
4. 4
   ЭкстракцияExtract with diethyl ether (×3)
5. 5
   ПромывкаCombine extracts and wash with saturated aqueous sodium chloride solution
6. 6
   Сушкаdry (magnesium sulfate)
7. 7
   Фильтрацияfilter
8. 8
   Концентрированиеconcentrate
9. 9
   Другоеpurify
10. 10
    Промывка(silica gel chromatography, eluting with 0:100 to 1:1 ethyl acetate:hexanes)

Методика

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%).

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