反应 #742287

反应方程式

1,4-Dimethyl-bicyclo[3.2.1]octan-3-one

NaBH4

→

1,4-dimethyl-bicyclo[3.2.1]octan-3-ol

收率 95.2%

溶剂

isopropanol

反应条件

后处理

1. 1
   温度refluxed for 30 minutes
2. 2
   其他quenched with acetone
3. 3
   其他The organic layer was separated
4. 4
   浓缩concentrated

实验过程

1,4-Dimethyl-bicyclo[3.2.1]octan-3-one (160 g, 1.05 mol, obtained as above in EXAMPLE III) was added to a NaBH4 suspension (12 g, 0.33 mol) in isopropanol (200 mL), and refluxed for 30 minutes. The reaction mixture was cooled to room temperature, and quenched with acetone followed by acetic acid. The organic layer was separated and concentrated to provide crude 1,4-dimethyl-bicyclo[3.2.1]octan-3-ol (150 g, 1.0 mol), which was then added to dimethyl carbonate (CO(OCH3)2, 270 g, 3 mol), and potassium tert-butoxide ((CH3)3COK, 25 g), and refluxed for 3 hours. The volatile ingredients were removed with a Dean Stark trap. The reaction mixture was subsequently quenched with acetic acid, and washed with water. Fractional distillation of the organic layer provided carbonic acid 1,4-dimethyl-bicyclo[3.2.1]oct-3-yl ester methyl ester (125 g) having a boiling point of 65° C. at a pressure of 0.5 mmHg

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