Dimethylformamide → 2-Methylpentane

Participants

Reaction Steps

3-Phenethyloxypropanoic acid (0.25 g) was dissolved in dichloromethane (8 mL) and treated with oxalyl chloride (0.22 g) and a drop of dimethylformamide at ambient temperature. The resultant solution was stirred at ambient temperature for 1 hour. The solution was then concentrated and azeotroped with dichloromethane (3×8 mL). The collected residue was dissolved in dichloromethane (8 mL) and added to a stirred solution of N-(2,2-diethoxyethyl)aniline (0.27 g) and N-ethyl-N-isopropyl-propan-2-amine (0.4 mL), dissolved in dichloromethane (4 mL), at ambient temperature. The resultant solution was stirred at ambient temperature for 1 hour. The mixture was then poured into ethyl acetate (25 mL), washed with water (2×25 mL), washed with brine (25 mL), dried over anhydrous magnesium sulphate, filtered and concentrated. The collected residue was purified by flash chromatography eluting with 1:6 ethylacetate:iso-hexane to yield the sub-titled compound (0.18 g) as an oil.

Provenance & Evidence