1-Octene → HCID 57887315, compound

Participants

Reaction Steps

To a stirring solution of 1-octene (0.032 g, 0.3 mmol, 1.4 eq) in tetrahydrofuran (1 ml) under argon at 0° C. was added 9-BBN in tetrahydrofuran (0.5M, 0.6 ml, 0.3 mmol, 1.5 eq). The reaction was stirred for 7 hours then 6-bromo-7-ethyl-3-hydroxy-2-(4-benzyloxy-3,5-dimethoxy-phenyl)-chromen-4-one 57 (0.102 g, 0.2 mmol) in tetrahydrofuran (4 ml), 3M NaOH solution (0.2 ml) and dichloropalladium(dppf) (0.005 g, 0.006 mmol, 0.03 eq) were added and the reaction heated to reflux for 15 hours. The reaction was then quenched with water and diethyl ether and acidified (6 M HCl). The organic layer was collected and the aqueous layer extracted with dichloromethane. The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo to give a red oil.

Provenance & Evidence