HCID 11076344, compound → HCID 11097971, compound

Participants

Reaction Steps

To the pre-cooled solution of 0.55 M NaOCl (110 mL, 60.0 mmol) and 0.05 M Na2HPO4 (43 mL) at 0° C., was added (2S)-2-dimethoxymethyl-2-methyl-6-nitro-2H-1-benzopyran (4 g, 15 mmol) and (R,R) Jacobson's catalyst (477.5 mg, 0.75 mmol) in CH2Cl2 (20 mL). The reaction mixture was stirred at rt for 8 hr and then filtered through Celite to remove the jacobson's catalyst. The layer was separated and the organic layer was washed with brine, dried (Na2SO4), filtered, then concentrated under reduced pressure. The residue was purified by silicagel column chromatography (n-hexane:ethyl acetate=4:1) to give the desired compound (3.24 g, 77%) as a light yellow solid.

Provenance & Evidence