Nitrogen → (2-(Chloromethyl)oxazol-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 methyl 2-(chloromethyl)oxazole-4-carboxylate (Organic Process Research & Development 2001, 5, 37-44) (12.50 g, 71.20 mmol) in THF (400 mL) was treated dropwise at 0° C. with DiBAL-H (242 mL of a 1.0 M solution in THF, 242.0 mmol) and the resulting solution was stirred for 1 h at 0° C. and then allowed to warm to rt. The reaction mixture was carefully poured over a Rochelle's salt solution (600 mL) and EA (250 mL) was added. The mixture was stirred for 1.5 h. The aq. layer was extracted with EA (2×250 mL) and the combined org. layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure. Purification of the residue by FC (1:4 hept-EA) gave the title compound as a yellow oil: TLC: rf (1:4 hept-EA)=0.28. LC-MS-conditions 07: tR=0.39 min; [M+H]+=147.98.

Provenance & Evidence