Methyl morpholine oxide → HCID 86669880, compound

Participants

Reaction Steps

To 2-isopropoxy-5-(7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazol-3-yl)benzonitrile (Preparation 15C, 0.088 g, 0.247 mmol) in THF (1.5 mL) was added N-methylmorpholine-N-oxide (50% in water) (0.17 mL, 0.370 mmol) followed by osmium tetroxide (0.039 mL, 4.94 μmol) at room temperature. The contents were stirred at room temperature for 3.5 h. Sodium periodate (0.106 g, 0.494 mmol) dissolved in 0.5 mL of water was added over a period of 2 min. at room temperature and the contents were stirred at room temperature for 1 h. The reaction mixture was concentrated and partitioned between ethyl acetate (15 mL) and water (10 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated to yield 5-(7-formyl-4,5-dihydronaphtho[1,2-c]isoxazol-3-yl)-2-isopropoxybenzonitrile (0.090 g, 0.176 mmol, 71% yield) as an orange-yellow solid. LC/MS M+1=359.1.

Provenance & Evidence