Sodium cyanoborohydride → HCID 58443694, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(2,4-dichlorophenyl)-pentanal O-methyl-oxime (6.0 g, 23 mmol) in acetic acid (50 ml) was treated at 10° C. with sodium cyanoborohydride (2.90 g, 46 mmol) added in small portions over 10 minutes and the resulting solution was stirred at 24° C. for 4 hours. The solvent was evaporated under reduced pressure (co-evaporation with toluene twice) and the residue was slurried with water and pH was adjusted to 11 with 1M NaOH. The aqueous phase was extracted with dichloromethane (2×50 ml), washed with brine and dried over anhydrous Na2SO4. After removal of the solvent (100 mbar; 45° C.), the residue (6.2 g) was purified by flash chromatography over silica gel (250 g; eluent: c-hexane). 5.15 g (79.0% of theory) of N-[2-(2,4-dichlorophenyl)-pentyl]-O-methyl-hydroxylamine was obtained in form of a clear liquid.

Provenance & Evidence