Triethylamine → HCID 10572652, compound

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Reaction Steps

2-Dimethylamino-2-(2-thienyl)-1-butanol (8 g), triethylamine (4.85 g) and dimethylaminopyridine (catalytic amount) are dissolved in tetrahydrofuran (10 ml), and 3,4,5-trimethoxybenzoyl chloride (11.1 g) is gradually added to the solution under ice-cooling. The mixture is stirred at room temperature for 16 hours and concentrated under reduced pressure to remove solvent. The residue is dissolved in diluted hydrochloric acid, and the solution is washed with ether. The solution is alkalized with potassium carbonate and extracted with ethyl acetate. The extract is washed with an aqueous saturated sodium chloride solution, dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel column chromatography (solvent, n-hexane:ethyl acetate=5:2), whereby 2-dimethylamino-2-(2-thienyl)-butyl 3,4,5-trimethoxybenzoate (12.8 g) is obtained as colorless oil.

Provenance & Evidence