Hydrochloric Acid → HCID 22010409, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl (RS)-4-[2-acetyl-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)-butanoate (0.5 g) in ethanol (5 mL) is treated with pyridine-2-carboxaldehyde (0.12 g) and aqueous sodium hydroxide solution (0.95 g; 33% w/w) and stirred at 25° C. for 90 minutes. The solution is diluted with water and then brought to pH 7 by treatment with hydrochloric acid (2 M), forming a yellow gum. This gum is extracted with ethyl acetate, and the extract is washed with water, dried and evaporated. The resulting residue is subjected to flash chromatography on silica gel, eluting with a mixture of ethyl acetate and pentane (65:35 v/v), followed by trituration with pentane, to give (E)-(RS)-4-(2-methylphenyl)-4-[2-{3-(2-pyridyl) prop-2-enoyl}-5-(3-thienylmethoxy)phenoxy]butanoic acid (0.22 g) in the form of a yellow solid, m.p. 65-70° C. [NMR(CDCl3):- 2.1-2.9 (4H,m),2.4(3H,s),4.9(2H,q),5.6(1H,q), 6.2-7.6(12H),7.7(1H,d,J=16 Hz),7.8(1H,t), 8.0(1H,d,J=16 Hz),8.6(1H,d)].

Provenance & Evidence