1,3-Oxazole-2-carboxaldehyde → Oxazol-2-yl(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)methanol

Participants

Reaction Steps

4-(2-Tetrahydro-3H-pyranoxy)phenylmagnesium bromide (0.5 M in THF, 6.7 mmol) was added dropwise to a solution of oxazole-2-carbaldehyde (5.15 mmol) in THF (8 mL). After stirring at room temperature for 2.5 hours, the reaction was quenched with water, extracted with EtOAc (200 mL), the organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed (silica gel, 1:2 EtOAc/hexane) to obtain compound 10.1 (3.1 mmol). MS ESI (pos.) m/e:276(M+H). 1H NMR (400 MHz) (DMSO-d6) δ 8.02 (s, 1H); 7.31 (d, J=8.7 Hz, 2H); 7.14 (s, 1H); 6.97-7.01 (m, 2H); 6.27 (d, J=5 Hz, 1H); 5.74 (d, J=5 Hz, 1H); 5.44 (s, 1H); 3.74 (m, 1H); 3.52 (M, 1h); 1.72-1.81 (m, 3H); 1.52-1.60(m, 4H).

Provenance & Evidence