Pyridine → 12-Methoxycarbonyloxy-15-pentadecanolide

Participants

Reaction Steps

480 g (1.89 mol) of 12-hydroxy-15-pentadecanolide (VII) are dissolved in 900 ml of methylene chloride with 205.5 g of pyridine. 213 g (2.2 mol) of methyl chloroformate in 900 ml of methylene chloride are added dropwise to this mixture at 0° to 5° C. in the course of 1 hour. The reaction mixture is stirred at room temperature for a further 5 hours. The organic phase is washed neutral and dried over Na sulphate. The organic phase is freed from methylene chloride and subjected to fractional distillation. 540 g of 12-methoxycarbonyloxy-15-pentadecanolide are obtained; yield: 91% of theory.

Provenance & Evidence