Water → 4-Chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-2-carboxylic acid

HRID 1874962ノート

反応式

HRID 1874962 の反応式
[O-][Mn](=O)(=O)=O.[K+].O.[Cl:8][C:9]1[CH:13]=[C:12]([CH:14]=[O:15])[NH:11][C:10]=1[C:16]([O:18][CH3:19])=[O:17].[OH:20]S([O-])=O.[Na+]>CC(C)=O.Cl>[Cl:8][C:9]1[CH:13]=[C:12]([C:14]([OH:20])=[O:15])[NH:11][C:10]=1[C:16]([O:18][CH3:19])=[O:17]

参加物

7

反応物 4

HCID 962WaterHCID 516875Potassium PermanganateHCID 23665763Sodium BisulfiteHCID 86644900methyl 3-chloro-5-formyl-1H-pyrrole-2-carboxylate

生成物 1

HCID 684860074-Chloro-5-[(methyloxy)carbonyl]-1H-pyrrole-2-carboxylic acid収率 82%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒2 回HCID 313Hydrochloric Acid溶媒

実験手順

KMnO4 (2.53 g, 16.0 mmol) was dissolved in acetone and water and added dropwise over a 2 hr period to a solution of methyl 3-chloro-5-formyl-1H-pyrrole-2-carboxylate (1.50 g, 8.00 mmol) in acetone (250 mL). After stirring for 4 hr the solution was poured into a solution of NaHSO3 in 1N HCl. This was extracted with EtOAc and the organic layer was washed with water. The organic layer was dried over MgSO4 and evaporated to afford the title compound (1.33 g, 82%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.15 (br. s., 1H), 12.75 (br. s., 1H), 6.78 (d, 1H), 3.77 (s, 3 H). LCMS: m/z 203.9 (M+1).

後処理

  1. extractionThis was extracted with EtOAc
  2. washthe organic layer was washed with water
  3. dry with materialThe organic layer was dried over MgSO4
  4. customevaporated

出典と根拠

ORDレコード
ord-e2e7ccbcfda8417bb9077cba948c64a1
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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