Boron tribromide → 5,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl ethyl ketone

Participants

Reaction Steps

To a solution of 1-(3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one (Intermediate 12, 2.07 g, 7.9 mmol) in CH2Cl2 (40 mL) at 0° C. was added BBr3 (8.9 mL, 1M in CH2Cl2 8.9 mmol) dropwise. After 30 min, the reaction was quenched with ice-H2O, and extracted with EtOAc. The organic layer was washed with brine, dried-over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (2% EtOAc-hexane) to give the title compound as a white solid (2.6 g, 90%).

Provenance & Evidence