Dimethylformamide → HCID 67311651, compound

Participants

Reaction Conditions

Reaction Steps

In methylene chloride (50 mL) was placed 2-methyl-5-nitrobenzoic acid (3.00 g, 16.6 mmol) and 1 microdrop of dimethylformamide. The solution was cooled to 0° C. and to this was added oxalyl chloride (3.15 g, 24.8 mmol). After 15 minutes the mixture was allowed to warm to RT and stirred a further 2 hours. The mixture evaporated at reduced pressure. This residue was dissolved in THF (60 mL) and cooled to 0° C. To this was added the 2.00N TMS-diazomethane (18.6 mL, 37.3 mmol) and the mixture stirred at 0° C. for 5 hrs. The solution was evaporated at reduced pressure and the new residue was treated with benzyl alcohol (15 mL) and 2,4,6-collidine (10 mL) and warmed to 180° C. for 15 min. After cooling to RT and diluting with ethyl acetate (100 mL), the resulting solution was washed successively with water (2×100 mL), 5% citric acid (100 mL, till pH of aqueous phase is acidic), water (100 mL) and brine (100 mL). The solvent was removed at reduced pressure and the resultant oil was dried on the high vacuum line at 65° C. to remove most excess benzyl alcohol. The oil was purified by chromatography (Biotage Si-40 column, 10-40% ethyl acetate/Hex—1398 mL) to give benzyl 2-(2-methyl-5-nitrophenyl)acetate as an oil (2.465 g, 52% yield) which was used as is.

Provenance & Evidence