反应 #1771994

反应方程式

1-methyl-1-hydroxycarbonylcyclohexane

diborane

→

1-methyl-1-hydroxymethylcyclohexane

收率 69.0%

溶剂

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   其他The cooling bath was removed
2. 2
   其他The remaining borane was quenched by the slow addition of saturated sodium bisulfate (10 mL) over 90 min
3. 3
   温度with cooling
4. 4
   workup.ADDITIONAdditional saturated sodium bisulfate (200 mL) was added and after 20 min
5. 5
   workup.STIRRINGof stirring the aqueous layer
6. 6
   其他was removed
7. 7
   洗涤The organic layer was washed with water and saturated sodium chloride
8. 8
   其他dried
9. 9
   过滤filtered
10. 10
    浓缩concentrated
11. 11
    其他The residue was purified by flash chromatography

实验过程

To a solution of 1-methyl-1-hydroxycarbonylcyclohexane (10 g, 70 mmol) in tetrahydrofuran(300 mL) at 0° C. was added 1M diborane in tetrahydrofuran (200 mL, 200 mmol) over 90 minutes. The cooling bath was removed and the reaction mixture was stirred at room temperature for two days. The remaining borane was quenched by the slow addition of saturated sodium bisulfate (10 mL) over 90 min with cooling. Additional saturated sodium bisulfate (200 mL) was added and after 20 min of stirring the aqueous layer was removed. The organic layer was washed with water and saturated sodium chloride, dried, filtered and concentrated. The residue was purified by flash chromatography using 20% diethylether in hexanes to give 1-methyl-1-hydroxymethylcyclohexane (6.17 g, 48 mmol, 69%).

来源