Diisobutylaluminum hydride → 6-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one

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Reaction Steps

A solution of methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-carboxylate (30 g, 0.145 mol) in dry CH2Cl2 (500 mL) was cooled to −78° C. and added DIBAL-H (51 g, 0.36 mol) over a period of 45 min and then stirred at the same temperature for 14 h. The reaction mixture was quenched with 1.5N HCl and filtered off the solid product. The solid compound was dried under vacuum to give 6-(hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one (18 g, 69%).

Provenance & Evidence