反应详情

To a stirring solution of 4-methyl pent-1-ene (0.110 g, 1.3 mmol, 1.4 eq) in tetrahydrofuran (2 ml) under argon at 0° C. was added 9-BBN in tetrahydrofuran (0.5M, 2.7 ml, 1.4 mmol, 1.5 eq). The reaction was allowed to warm to room temperature then stirred for 6 hours then 34 (0.499 g, 0.9 mmol) (prepared as described in Example 2) in tetrahydrofuran (5 ml), 3M NaOH solution (1.1 ml) and dichloropalladium (dppf) (0.028 g, 0.03 mmol, 0.04 eq) were added and the reaction heated to reflux for 14 hours. The reaction was then quenched with water and diethyl ether. The organic layer was collected and the aqueous layer extracted with diethyl ether (2×). The combined organic layers were washed with 1M HCl and brine then dried (MgSO4) and concentrated in vacuo to give a yellow oil. A silica plug (dichloromethane) yielded 39e* (0.197 g, 49%) as a yellow oil.

1. temperaturethe reaction heated
2. temperatureto reflux for 14 hours
3. customThe reaction was then quenched with water and diethyl ether
4. customThe organic layer was collected
5. extractionthe aqueous layer extracted with diethyl ether (2×)
6. washThe combined organic layers were washed with 1M HCl and brine
7. dry with materialthen dried (MgSO4)
8. concentrationconcentrated in vacuo
9. customto give a yellow oil
10. customA silica plug (dichloromethane) yielded 39e* (0.197 g, 49%) as a yellow oil