反应详情

To an ice-cold solution of 4-formyl-bicyclo[3.2.1]octane-1-carboxylic acid ethyl ester (3.85 mmol, 0.81 g) was added slowly Jones reagent (2.7 M, 1.43 mL). The reaction was stirred at ice temperature 20 min. then quenched by addition of iPrOH. diluted with H2O and extracted with Et2O (3×). The combined organic extracts were washed with H2O (2×). brine (1×), and dried (MgSO4). Filtration and evaporation provided the viscous oily bicyclo[3.2.1]octane-1,4-dicarboxylic acid 1-ethyl ester (0.76 g, 87%) as a mixture of axial and equatorial acids. 13CNMR (100 MHz, CDCl3): 14.16 (q), 19.86 (t), 21.07 (t), 25.98 (t), 29.20 (t), 31.52 (t), 31.87 (t), 32.27 (t). 33.39 (t), 37.80 (d), 38.07 (t), 38.10 (d), 42.06 (t). 44.80 (d), 45.78 (d), 49.38 (s), 49.60 (s), 60.31 (t), 60.36 (t), 177.08 (s), 180.0.1 (s).

1. customthen quenched by addition of iPrOH
2. additiondiluted with H2O
3. extractionextracted with Et2O (3×)
4. washThe combined organic extracts were washed with H2O (2×)
5. dry with materialbrine (1×), and dried (MgSO4)
6. filtrationFiltration and evaporation