반응 #742287

반응 방정식

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

NaBH4

→

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

수율 95.2%

용매

isopropanol

반응 조건

후처리

1. 1
   온도refluxed for 30 minutes
2. 2
   기타quenched with acetone
3. 3
   기타The organic layer was separated
4. 4
   농축concentrated

실험 절차

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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