2-(3-Bromophenoxy)tetrahydro-2H-pyran → 2(3-Hydroxy-3-(3-(2-tetrahydropyranyloxy)phenyl)propyl)benzoic acid

Participants

Reaction Steps

At -10° C., a solution of the aldehyde of Step 2 (5.045 g, 28.3 mmol) in 50 mL of THF was added dropwise to 0.57M 3-(2-tetrahydropyranyloxy)phenylmagnesium bromide in THF (120 mL, 68.4 mmol, prepared from 2-(3-bromophenoxy)tetrahydropyran and Mg in THF and filtered to remove the excess of Mg) and the mixture was stirred at r.t. for 30 min. At 0° C., 25% aq NH4OAc was added. The title product was extracted with EtOAc, dried over Na2SO4 and purified by flash chromatography on silica using acetone:toluene:AcOH 5:95:1 and 15:85:1. Yield: 9.74 g, 97%.

Provenance & Evidence