Tetrahydrofuran → Oxazol-5-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanol

Participants

Reaction Conditions

Reaction Steps

4-(2-Tetrahydro-3H-pyranoxy)phenylmagnesium bromide (120 mL, 0.5 M in THF, 60 mmol) was added dropwise to a solution of oxazole-4-carbaldehyde (4.85 g, 50 mmol) in THF (90 mL) at −78° C. After stirring at −78° C. for 21 hours, the reaction was quenched with saturated NH4Cl (aq) and warmed to room temperature. The mixture was extracted with EtOAc (500 mL), the organic phase was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give 17 g of the crude product 75.1, which was used in the next reaction without further purification.

Provenance & Evidence