Diethyl Ether → 1-(3-(((2-Tetrahydropyranyl)oxy)methyl)phenyl)-2-propen-1-ol

Participants

Reaction Conditions

Reaction Steps

To the aldehyde of Step 10 (85 g, 386 mmol) in toluene (1 L) at 0° C. was slowly added vinyl magnesium bromide in Et2O (450 mL, 1M, 450 mmol) over a 30 minute period. After stirring for 1 hr at 0° C., the reaction mixture was quenched with 25% aq. NH4OAc and extracted with EtOAc (3×). Evaporation and purification by flash chromatography (15%→25% EtOAc in toluene) yielded 82 g (86%) of the title compound.

Provenance & Evidence