Nitrogen → (E)-(2-Styryloxazol-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of (E)-ethyl 2-styryloxazole-4-carboxylate (WO 2009077990 A1) (8.5 g, 34.9 mmol) in THF (28.3 mL) was treated dropwise at 0° C. with DiBAL-H (85.0 mL of a 1.0 M solution in toluene, 85.0 mmol) and the resulting solution was stirred for 1.5 h at 0° C. Rochelle's salt solution was added followed by EA and the mixture was stirred for 24 h at rt. The aq. layer was extracted with EA (3×40 mL) and the combined org. layers were dried over Na2SO4, filtered and the solvent was removed under reduced pressure to give the title compound as an orange oil. TLC: rf (1:1 hept-EA)=0.20. LC-MS-conditions 07: tR=0.71 min, [M+H]+=202.15.

Provenance & Evidence