تفاعل #742288

معادلة التفاعل

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

NaBH4

→

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

المردود 88.8%

المذيبات

isopropanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةrefluxed for 30 minutes
2. 2
   أخرىquenched with acetone
3. 3
   أخرىThe organic layer was separated
4. 4
   تركيزconcentrated

الإجراء التجريبي

1,4-Dimethyl-bicyclo[3.2.1]octan-3-one (325 g, 2.14 mol, obtained as above in EXAMPLE III) was added to a a NaBH4 suspension (24 g, 0.64 mol) in isopropanol (600 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 (300 g, 1.9 mol), which was added to a solution of sodium amide (NaNH2, 94 g, 2.4 mol) in tetrahydrofuran (THF, 1 L) while at reflux, and aged for 5 hours. Allyl chloride (CH2CHCH2Cl, 170 g, 2.2 mol) was subsequently added at 45° C. and aged for another 2 hours. The reaction mixture was subsequently washed with water and a Na2CO3 solution. Fractional distillation of the organic layer provided 3-allyloxy-1,4-dimethyl-bicyclo[3.2.1]octane (220 g) having a boiling point of 120° C. at a pressure of 30 mmHg

المصدر