Dichloromethane → 3-Benzyloxy-7-hexyl-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one

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Reaction Steps

To a stirring solution of 1-hexene (0.109 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 and stirred for 8 hours then 34 (0.505 g, 0.9 mmol) (produced as described in Example 2) in tetrahydrofuran (5 ml), 3M NaOH solution (1.1 ml) and dichloropalladium (dppf) (0.032 g, 0.04 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 39e (0.112 g, 24%) as a colourless oil.

Provenance & Evidence