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ethyl 3-[(tetrahydropyran-2-yl)oxy]bicyclo[3.1.0]hexane-6-carboxylate

Ethyl 3-[(tetrahydropyran-2-yl)oxy]bicyclo[3.1.0]-hexane-6-carboxylate

sodium methoxide

→

methyl 3-[(tetrahydropyran-2-yl)oxy]bicyclo[ 3.1.0]-hexane-6-carboxylate

용매

methanol

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후처리

1. 1
   workup.ADDITIONa mixture of exo and endo isomers in a 4:1 ratio
2. 2
   workup.ADDITIONof the above mixture of isomers and 150 mg
3. 3
   온도under reflux for 4 hrs
4. 4
   기타The mixture then is evaporated
5. 5
   추출the residue extracted with diethyl ether
6. 6
   추출the diethyl ether extract
7. 7
   기타evaporated

실험 절차

Gas-liquid chromatographic analysis of the ethyl 3-[(tetrahydropyran-2-yl)oxy]bicyclo[3.1.0]hexane-6-carboxylate (VIII) obtained as above shows that the product is a mixture of exo and endo isomers in a 4:1 ratio. A solution of 2.8 g. of the above mixture of isomers and 150 mg. of sodium methoxide in 50 ml. of methanol is heated under reflux for 4 hrs. The mixture then is evaporated, the residue extracted with diethyl ether, and the diethyl ether extract evaporated to give the exo isomer of methyl 3-[(tetrahydropyran-2-yl)oxy]bicyclo[ 3.1.0]-hexane-6-carboxylate as an oil; b.p. 130°-133° at 1.1 mm.; homogenous as to the exo isomer by gas-liquid chromatographic analysis and by thin layer chromatographic analysis (silica, developed with benzene-ether 5:1).

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