ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Furan derivatives. CIII. Nitration of methyl 3-(5-nitro-2-furyl)acrylate

J. Kováč and D. Végh

Department of Organic Chemistry, Slovak Technical University, 880 37 Bratislava

Abstract:  Nitration of methyl 3-(5-nitro-2-furyl)acrylate with fuming nitric acid afforded 5-nitro-2-furancarboxylic acid (II) as a main product (70%) and 5-nitro-2-furaldehyde (III) and methyl ester of 2-nitro-3-(5-nitro-2-furyl)acrylic acid /V as by-products. The nitration of methyl ester of / gave at — 10°C the corresponding methyl ester of IV in a 29% yield, whereas the nitration with a solution of N₂0₄ in CCl₄ furnished methyl ester of IV even in a better yield. Both procedures led prevalently to the Z configuration of the ester of IV.

Full paper in Portable Document Format: 323a386.pdf

Chemical Papers 32 (3) 386–391 (1978)