3-Chloro-1H-Pyrrole-2-carboxaldehyde synthesis
- Product Name:3-Chloro-1H-Pyrrole-2-carboxaldehyde
- CAS Number:56164-42-2
- Molecular formula:C5H4ClNO
- Molecular Weight:129.54
1121-76-2
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Yield:56164-42-2 48%
Reaction Conditions:
with copper(ll) sulfate pentahydrate in water at 20; for 24 h;Irradiation;
Steps:
Aldehyde 4a: 3-chloro-1H-pyrrole-2-carbaldehyde
To a stirring solution of 4-chloropyridine N-Oxide (30.2 mg, 230 mmol) and copper sulfate pentahydrate (600 mg, 3.75 mmol) in distilled water (25 mL) was irradiated for 24 h with a 110W low pressure Hg lamp at room temperature. Then the mixture was extracted with EtOAc (500 mL × 2), and the organic layer was dried over Na2SO4, concentrated under reduced pressure. The residue was purified by PTLC (hexane/EtOAc = 5/1) to give 4a (13.8 mg, 110 mmol, 48) as a yellow solid. 1H-NMR (500 MHz, CDCl3) d 9.67 (s, 1H), 9.21 (br, 1H), 7.02-7.01(m, 1H), 6.29-6.28(m, 1H). 13C-NMR (126 MHz, CDCl3) d 177.6, 127.8, 125.6, 125.4, 111.7. HR- ESI-MS: m/z: [M+H]+ calculated for C5H5ClNO, 130.0060; found, 130.0042.
References:
Yoshida, Chihiro;Higashi, Tomoya;Hachiro, Yoshifumi;Fujita, Yuki;Yagi, Takuya;Takechi, Azusa;Nakata, Chihiro;Miyashita, Kazuya;Kitada, Nobuo;Saito, Ryohei;Obata, Rika;Hirano, Takashi;Hara, Takahiko;Maki, Shojiro A. [Bioorganic and Medicinal Chemistry Letters,2021,vol. 37,art. no. 127837] Location in patent:supporting information
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