2-[(3-Bromophenyl)methoxy]oxane → 2-(3-Hydroxy-3-(3-((2-tetrahydropyranyloxy)methyl)phenyl)propyl)benzoic acid

Participants

Reaction Steps

At -10° C., a solution of the aldehyde of Step 4 (5.045 g, 28.3 mmol) in 50 mL of THF was added dropwise to 0.57M 3-((2-tetrahydropyranyloxy)methyl)phenylmagnesium bromide in THF (120 mL, 68.4 mmol, prepared from the bromide of Step 2 and Mg in THF and filtered to remove the excess of Mg) and the mixture as 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: HOAc 5:95:1 and 15:85:1.

Provenance & Evidence