2,4,6-Trimethylpyridine → 2-[4-chloro-(Z)-2-buten-1-yloxy]acetic Acid Tert-Butyl Ester

Participants

Reaction Steps

To a solution of 420 mg of 2-[4-hydroxy-(Z)-2-buten-1-yloxy]acetic acid tert-butyl ester in 10 ml of N,N-dimethylformamide, 1.00 g of 2,4,6-collidine and 350 mg of lithium chloride were added. While stirring under ice cooling, 0.64 ml of methanesulfonyl chloride was added dropwise, followed by stirring at room temperature for 2 hours. The reaction solution was extracted with ethyl acetate after adding iced water, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 350 mg of the desired compound as a colorless oily substance.

Provenance & Evidence