Hydrochloric Acid → (+/-) Methyl alpha-(7-Hydroxy-4,5,6,7-tetrahydro-5-thieno[3,2-c]pyridyl)-o-chlorophenylacetate

関与物質

反応手順

5-(2-thienyl)-3-(methoxycarbonyl-o-chlorobenzyl)-1,3-oxazoline (22) (5 g, 14.7 mmol) was dissolved in 5 mL of dry DMF and the solution was added dropwise at 0-5° C. over HCl in dry DMF. The reaction was subsequently allowed to warm to room temperature and stirred to complete transformation of the starting material. The solution was partitioned between 1 M sodium bicarbonate solution and toluene. The organic phase was dried on sodium sulfate filtered through a plug of silica gel and evaporated under vacuum to yield 4.3 g of product. 1H-NMR (CDCl3, ppm) 7.45-7.55 (1H, m), 7.35-7.45 (1H, m), 7.2-7.35 (2H, m), 7.2 (1H, d), 6.68 (1H, dd), 5.09 and 5.03 (1H, 2 s), 4.68 (1H, bs), 3.5-4.0 (5H, m), 2.7-3.2 (3H, m).

情報源と証拠