反応 #44507

反応方程式

product

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

Potassium tert-butoxide

tosylmethyl isocyanide

methanol

→

title compound

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

溶媒

DME

DME

反応条件

後処理

1. 1
   workup.WAITAfter ten minutes
2. 2
   温度heated (45° C.) for thirty minutes
3. 3
   温度After cooling
4. 4
   その他the reaction mixture was partitioned with diethyl ether and water
5. 5
   洗浄The organic phase was washed with brine
6. 6
   乾燥dried (MgSO4)
7. 7
   ろ過filtered
8. 8
   その他evaporated
9. 9
   その他The residue was purified over silica gel using 2-10% diethyl ether in hexanes

実験手順

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.

出典