Acetic Acid → Ethyl 3,4,5-trimethyl-1H-pyrrole-2-carboxylate
Reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH3:10])[C:6]=1[C:7](=O)C.I.[CH2:12]=[O:13].[C:14](O)(=[O:16])[CH3:15]>>[CH3:1][C:2]1[NH:3][C:4]([C:12]([O:16][CH2:14][CH3:15])=[O:13])=[C:5]([CH3:10])[C:6]=1[CH3:7]Participants
5
Procedure
2,4-Dimethyl-3-acetyl-pyrrole (0.68 g), acetic acid (15 ml), aq. hydriodic acid (15 ml) and paraformaldehyde (0.6 g) were stirred for three hours under nitrogen at room temperature. The crude product was isolated as in Example 4 (2,3,4-trimethyl-5-carbethoxy-pyrrole) then crystallized from benzene to yield 0.55 g (73%) of colourless elongated prisms, m.p. 204°-207° C. (lit. 207° H. Fischer and W. Zerweck, Berichte 56, 523 (1923)). Anal. Calc. for C9H13NO: C, 71.49; H, 8.67; N, 9.26. Found: C, 71.29; H, 8.68; N, 9.38.
Sources & evidence
- ORD record
- ord-6a1097aaed8341959445efbc1e49a907
- Source dataset
- uspto-grants-1978_01
- Patent number
- US04070366
Reaction notes
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