Triethylamine → HCID 21841052, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (-8° C.), stirred suspension of 2,5-dihydroxybenzaldehyde (13 g, 93.6 mmol) in of CH2Cl2 (65 ml) (dried over 4A sieves) (65 ml) was added triethylamine (6.5 ml, 46.8 mmol) to give a deep red solution. Pivaloyl chloride (5.6 g, 46.8 mmol) was added portionwise keeping the temperature below 0° C. After the addition was complete the reaction was allowed to warm to ambient temperature and stirred overnight. The reaction was washed with 2N aqueous HCl, water, saturated aqueous NaHCO3 and dried (MgSO4). The organic solution was filtered and evaporated and the residue purified by chromatography (eluant: CH2Cl2 /hexane) to give the title product as a colourless oil which crystallized on standing (4.7 g, 45% based on limiting reagent).

Provenance & Evidence