Sodium borohydride → HCID 10495522, compound

Participants

Reaction Steps

To a yellow suspension of Hg(OAc)2 (6.36 g, 19.94 mmol, 1.0 equiv) in THF/water (25 mL/ 30 mL) is added 4-bromo-2-tert-butyl-1-(3-methyl-2-butenyloxy)benzene (5.93 g, 19.94 mmol) in THF (5 mL) dropwise and stirred at room temperature for 4 h. To the resulting pale yellow solution is added NaOH (15 mL, 3M) followed by NaBH4 (0.75 g, 19.94 mmol, 1.0 equiv) in NaOH (5 mL, 3M). The resulting ash colored suspension is stirred at room temperature for 30 min, diluted with hexanes, and washed with water, saturated aq. NH4Cl and brine. The aqueous layers are extracted with hexanes; the combined organic layers are dried (MgSO4), filtered and concentrated. The residue is purified by flash column chromatography on silica (hexanes/EtOAc; 101->311) to give the title compound (4.21 g, 67%) as an oil.

Provenance & Evidence