Acetic Acid → 2-(2,3-Dihydrobenzofuran-5-yl)-2-hydroxyacetic acid

Participants

Reaction Conditions

Reaction Steps

α-Amino(2,3-dihydro-5-benzofuranyl)acetic acid (200 mg, 1.04 mmole) is dissolved in 250 mg (4.14 mmole) of glacial acetic acid and 145 mg (2.08 mmole) of sodium nitrite in about 5 ml of water is added dropwise. An additional 1 ml of glacial acetic acid is added and the mixture is heated to 65° C. and held at 65° C. for 4 hours. After cooling the reaction mixture is diluted with water and extracted with ethyl acetate for several hours. The ethyl acetate is dried over magnesium sulfate, filtered and evaporated to give a 65% yield of the title compound. NMR(DMSO-D6)ppm(δ)7.15(m,3); 5.18(d,1); 4.78(t,2) and 3.34(t,2).

Provenance & Evidence