Water → HCID 53927100, compound

Participants

Reaction Steps

A suspension of isochroman-3,4-dione 4-oxime (90.4 HPLC-area %, 145.8 g, 0.74 mol) and potassium carbonate (153.4 g, 1.11 mol) in toluene (1000 mL) was stirred at ambient temperature for 1 h before dimethylsulfate (141.4 g, 1.11 mol) was added dropwise at 26° C. over a period of 2.5 h. The resulting mixture was stirred for 24 h at ambient temperature. After completion of the reaction, dist. water (1000 mL) was added to the mixture under stirring. The organic layer was separated, washed with dist. water (500 mL) and dried in vacuo at 30-50 mbar and max. 50° C. Isochroman-3,4-dione 4-(O-methyl-oxime) was obtained as a light orange solid (160.1 g, 88.7 HPLC-area %, quant. yield, diastereomeric ratio=58:42).

Provenance & Evidence