Dichloromethane → HCID 57887356, compound

Participants

Reaction Steps

To a stirring solution of 1-decene (0.176 g, 1.3 mmol, 1.4 eq) in tetrahydrofuran (2 ml) under argon was added 9-BBN in tetrahydrofuran (0.5M, 2.7 ml, 1.4 mmol, 1.5 eq). The reaction was stirred for 6 hours then 35 (0.560 g, 0.9 mmol) in tetrahydrofuran (5 ml), 3M NaOH solution (1.1 ml) and dichloropalladium (dppf) (0.027 g, 0.03 mmol, 0.04 eq) were added and the reaction heated to reflux for 15 hours. The reaction was then quenched with water and diethyl ether. The organic layer was collected and the aqueous layer extracted with dichloromethane. The combined organic layers were dried (MgSO4) and concentrated in vacuo to give a brown oil. Column chromatography (silica gel, DCM) yielded 40 g (0.339 g, 59%) as a pale yellow oil.

Provenance & Evidence