反应详情

Add borane-methyl sulfide complex (177 mL, 0.354 mol), slowly, by means of a dropping funnel, to a stirring solution of trans-cyclopropane-1,2-dicarboxylic acid monomethyl ester (Example 3a) (25.5 g, 0.177 mol), trimethyl borate (60.3 mL, 0.531 mol) and tetrahydrofuran (150 mL) at 0° C. After complete addition, allow the reaction to come to ambient temperature and stir for 2 h more. Pour the reaction mixture into a stirring solution of 50% aqueous sodium chloride solution (1.5 L)-concentrated HCl (10 mL). Extract the mixture with ethyl acetate (EtOAc) (3 times), combine the extracts, dry (Na2SO4) and concentrate the solvent to obtain a colorless oil: 22.6 g.

1. additionAdd borane-methyl sulfide complex (177 mL, 0.354 mol)
2. customat 0° C
3. additionAfter complete addition
4. customthe reaction
5. customto come to ambient temperature
6. extractionExtract the mixture with ethyl acetate (EtOAc) (3 times)
7. dry with materialdry (Na2SO4)
8. concentrationconcentrate the solvent
9. customto obtain a colorless oil