Methyl 4-methylbenzoate → HCID 67246324, compound

Participants

Reaction Conditions

Reaction Steps

1 g (5.81 mmol) of 4-bromo-2-methylpyridine and 1.75 g (11.60 mmol) of methyl 4-methylbenzoate are placed in a round-bottomed flask and dissolved in 30 ml of anhydrous tetrahydrofuran under a stream of nitrogen. The solution is cooled to 5° C. and 14 ml (14 mmol) of a lithium hexamethyldisilazane solution (1M in tetrahydrofuran) are added dropwise. After addition, the mixture is stirred at ambient temperature for 2 h 30 and then cooled to 5° C., before gradually adding 20 ml of water. The medium is subsequently diluted with 200 ml of ethyl acetate and 200 ml of water. The organic phase is separated, dried over sodium sulphate and filtered. 5 g of silica are subsequently added to the filtrate before concentrating it under reduced pressure. The powder obtained is used as solid deposit for chromatography on silica gel with a mixture of cyclohexane and ethyl acetate (95/5) as eluent. 1.03 g (61%) of compound are obtained in the form of a yellow powder.

Provenance & Evidence