تفاعل #44507

معادلة التفاعل

product

5-(tert-Butyl-dimethyl-silanyloxy)-cyclooctanone

Potassium tert-butoxide

tosylmethyl isocyanide

methanol

→

title compound

5-(tert-Butyl-dimethyl-silanyloxy)-cyclooctanecarbonitrile

المذيبات

DME

DME

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter ten minutes
2. 2
   درجة الحرارةheated (45° C.) for thirty minutes
3. 3
   درجة الحرارةAfter cooling
4. 4
   أخرىthe reaction mixture was partitioned with diethyl ether and water
5. 5
   غسيلThe organic phase was washed with brine
6. 6
   تجفيفdried (MgSO4)
7. 7
   ترشيحfiltered
8. 8
   أخرىevaporated
9. 9
   أخرىThe residue was purified over silica gel using 2-10% diethyl ether in hexanes

الإجراء التجريبي

Potassium tert-butoxide (30.4 mL, 1 M in tetrahydrofuran, 30.4 mmol) was added drop wise to a stirred and cooled (0° C.) solution of tosylmethyl isocyanide (4.74 g, 24.27 mmol) in dry DME (40 mL). After ten minutes, dry methanol (0.98 mL, 24.28 mmol) was added and followed by a solution of the product of Example 5B (3.11 g, 12.14 mmol) in DME (10 mL). The resulting solution was allowed to warm to room temperature and then heated (45° C.) for thirty minutes. After cooling, the reaction mixture was partitioned with diethyl ether and water. The organic phase was washed with brine, dried (MgSO4), filtered, and evaporated. The residue was purified over silica gel using 2-10% diethyl ether in hexanes to give the title compound as an oil.

المصدر