تفاعل #48663

معادلة التفاعل

tetrahydropyran-4-one

chloroacetonitrile

potassium tert-butoxide

→

desired compound

المردود 59.1%

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

المردود 59.1%

المذيبات

tert-butanol

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONadd
2. 2
   أخرىover 20 minutes
3. 3
   أخرىquench slowly with 1 N hydrochloric acid
4. 4
   استخلاصExtract with diethyl ether (×3)
5. 5
   غسيلCombine extracts and wash with saturated aqueous sodium chloride solution
6. 6
   تجفيفdry (magnesium sulfate)
7. 7
   ترشيحfilter
8. 8
   تركيزconcentrate
9. 9
   أخرىpurify
10. 10
    غسيل(silica gel chromatography, eluting with 0:100 to 1:1 ethyl acetate:hexanes)

الإجراء التجريبي

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%).

المصدر