Triethylamine → HCID 19348729, compound

Participants

Reaction Steps

15.5 ml (0.110 mol) of triethylamine and 616 mg '5.04 mmol) of 4-N,N-dimethylaminopyridine were added to a solution of 19.8 g (0.101 mol) of methyl 4-hydroxymethyl-2-methoxybenzoate [prepared as described in step (i) above] and 16.91 g (0.112 mol) of t-butyldimethylsilyl chloride in 150 ml of methylene chloride, and the resulting mixture was stirred for 2 hours. At the end of this time, the reaction mixture was diluted with a mixture of ethyl acetate and hexane, and the diluted mixture was washed with ice-cooled 1 N aqueous hydrochloric acid, with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, giving 32.20 g (a quantitative yield) of the title compound as an oily substance.

Provenance & Evidence