Chloroform → chloroform methanol water NH4OH

Participants

Reaction Steps

DMRIE-Ox (300 mg) was dissolved in 7 mL chloroform and washed with 3 mL 1N HCl. The organic phase was dried with MgSO4, then filtered into a reaction vessel. The solution was placed in an ice-water bath and N-hydrosuccinimide (82 mg) then dicyclohexylcarbodiimide (1.3 mL of a 0.5 M solution in dichloromethane) were added and the reaction was allowed to stir with warming for 8 hours. At this time propyl amine (40 mg) was added as a neat liquid and the reaction allowed to stir at room temperature overnight. The reaction was filtered, then evaporated. Chromatography of the filtrate residue through silica gel with CHCl3:MeOH:NH4OH:H2O (90:10:0.25:0.25) afforded pure product.

Provenance & Evidence