[(E)-1-(2-hydroxy-3-methylphenyl)ethylideneamino] acetate → 3,7-Dimethylbenzisoxazole

Participants

Reaction Conditions

Reaction Steps

(E)-1-(2-hydroxy-3-methylphenyl)ethanone O-acetyl oxime (Step 46.3) (6.0 g, 29.0 mmol) was dissolved in pyridine (60 mL) and the resulting mixture was heated up and stirred at 130° C. for 40 hr, cooled down to RT and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane/EtOAc 0-50% EtOAc) to afford the title product (3.62 g, 23.12 mmol, 80% yield) as pale yellow oil. tR: 0.96 min (LC-MS 2); ESI-MS: 148 [M+H]+; Rf=0.56 (hexane/EtOAc 3:1).

Provenance & Evidence