HCID 59051257, compound → HCID 86643254, compound

Participants

Reaction Steps

To a solution of 11-oxo-11H-dibenzo[b,e][1,4]dioxepine-4-carboxylic acid (256 mg, 1 mmol) in methylene chloride (15 ml) was added BH3-dimethyl sulfide complex (1.6 ml, 1 mol/L in methylene chloride) under ice bath. The mixture was stirred for 30 min at room temperature, refluxed for 5 h and then cooled. The reaction was quenched by addition of methanol, and the whole mixture was evaporated by a rotatory evaporator. The residue was diluted with saturated NaHCO3 (aq) and extracted with AcOEt. The organic layer was washed with saturated brine, dried over anhydrous MgSO4, purified by column chromatography and evaporated by a rotatory evaporator. To a solution of the crude product in CH2Cl2 (20 ml) was added a suspension of pyridinium chlorochromate (PCC, 280 mg, 1.3 mmol) and neutral Al2O3 (350 mg) in CH2Cl2 (20 ml) in ice bath under N2. The mixture was stirred for 18 h at room temperature, filtered, evaporated by a rotatory evaporator, purified by column chromatography to obtain 11-oxo-11H-dibenzo[b,e][1,4]dioxepine-4-carbaldehyde.

Provenance & Evidence