1-Decene → HCID 57887348, compound

Participants

Reaction Steps

To a stirring solution of 1-decene (0.189 g, 1.3 mmol, 1.4 eq) in tetrahydrofuran (2 ml) under argon was added 9-BBN in tetrahydrofuran (0.5M, 2.8 ml, 1.4 mmol, 1.5 eq). The reaction was stirred for 8 hours then 3-hydroxy-6-iodo-2-(4-benzyloxy-3,5-dimethoxy-phenyl)-chromen-4-one 56 (0.501 g, 0.9 mmol) in tetrahydrofuran (5 ml), 3M NaOH solution (1.26 ml) and dichloropalladium(dppf) (0.021 g, 0.03 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 diethyl ether (2×). The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo to give a red oil. This was passed through a short plug of silica, eluting with ethyl acetate to give 3-hydroxy-6-decyl-2-(4-benzyloxy-3,5-dimethoxy-phenyl)-chromen-4-one 58(0.369 g, 72%) as a red oil.

Provenance & Evidence