Water → HCID 15572418, compound

Participants

Reaction Steps

The starting material is prepared as follows: To the suspension of 32.7 g of 2-methyl-5-pyridinol in 400 ml of tetrahydrofuran, 400 ml of 1.6 molar n-butyllithium in hexane are added during 1 hour while stirring under nitrogen and cooling with ice to maintain the temperature below 10°. Thereupon 29 g of dimethylacetamide in 50 ml of tetrahydrofuran are added during 15 minutes, the mixture is stirred for 2 hours at room temperature and poured into 700 ml of water. It is thoroughly shaken, the aqueous layer separated, washed with diethyl ether, acidified with hydrochloric acid and again washed with diethyl ether. Its pH is adjusted to 5.0 with aqueous sodium bicarbonate and after saturation with sodium chloride the mixture is extracted with ethyl acetate-isopropanol (1:1). The extract is evaporated azeotropically with the aid of benzene and the residue is taken up in 100 ml of acetic anhydride. The mixture is stirred for 30 minutes at the steam bath, evaporated, the residue distilled and the fraction boiling at 130°-138°/0.9 mmHg collected, to yield the 5-acetoxy-2-pyridylacetone; its hydrochloride melts at 69°-72° and the oxime thereof at 149°-150°.

Provenance & Evidence