Hydrochloric Acid → HCID 22708189, compound

Participants

Reaction Steps

550 mg of 1,1-dimethylethyl 2-[(4-formylphenyl)thio]-2-methyl-propanoate and 381 mg of furfurylamine are initially charged in 100 ml of methanol and treated with 1 ml of glacial acetic acid. The mixture is stirred at room temperature for 15 min, briefly brought to the boil and then, at 0° C., admixed a little at a time with 493 mg of sodium cyanoborohydride. The mixture is stirred overnight at room temperature and then treated with 1 N HCl and stirred for 30 min. The mixture is then made basic using Na2CO3 solution and extracted 2× with ethyl acetate. The organic phase is washed (sat. NaCl solution) and dried (MgSO4). Concentration and chromatographic purification (dichloromethane/ethyl acetate 10+1) gives 430 mg of a colourless oil.

Provenance & Evidence