O-Methylhydroxylamine hydrochloride → HCID 72998856, compound

Participants

Reaction Steps

To a solution of 6-hydroxy-5,7-dimethylspiro[chromene-2,1′-cyclobutane]-3-carbaldehyde (421 mg, prepared as described in Example 19) in 8 mL of pyridine was added methoxyamine hydrochloride (628 mg). The reaction mixture was allowed to stir at room temperature overnight. The mixture was extracted with ethyl acetate and washed with 1N HCl. The organic solvent was evaporated in vacuo, the residue was purified by flash chromatography eluted with 10% ethyl acetate in hexane to give 6-hydroxy-5,7-dimethylspiro[chromene-2,1′-cyclobutane]-3-carbaldehyde O-methyloxime as a yellow solid. 1H-NMR (300 MHz, CDCl3) δ=7.82 (s, 1H), 6.68 (s, 1H), 6.60 (s, 1H), 4.45 (s, 1H), 3.98 (s, 3H), 2.75 (m, 2H), 2.44 (m, 2H), 2.40 (s, 3H), 2.22 (s, 3H), 1.98 (m, 2H) ppm. 13C-NMR (75 MHz, CDCl3) δ=148.6, 146.5, 146.4, 131.2, 125.8, 125.1, 119.9, 119.6, 116.0, 80.5, 62.1, 34.2, 16.6, 13.6, 11.4 ppm. MS: (m/z)=274.0 (M+H+).

Provenance & Evidence