Phenol → HCID 131719536, compound

Participants

Reaction Conditions

Reaction Steps

n-BuLi (2.4M in hexane, 674 μL, 1.62 mmol) was added dropwise (15 min.) to 2-bromopyridine (147 μL, 1.54 mmol) in THF (5 mL) at -78° C. and under Ar. The solution was stirred for 40 min. at this temperature. The 3-(tert-butyldiphenylsilyloxy)propiophenone (499 mg, 1.28 mmol) from Phenol 8, Step 3 in THF (2 mL) was then added dropwise (10 min.). The mixture was kept at -78° C. for 30 min. and allowed to warm to 0° C. After 20 min. the reaction was quenched with a saturated NH4Cl solution and extracted with EtOAc (3×). The combined organics were washed with 25% NH4OAc buffer, H2O, brine, dried (MgSO4) and concentrated to give an off-white gum, that was purified by column chromatography on silica gel (EtOAc/hexane 1:9), affording the title compound as a colorless gum (563 mg, 94%).

Provenance & Evidence