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

HRID 1874962노트

반응식

HRID 1874962 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매2회HCID 313Hydrochloric Acid용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e2e7ccbcfda8417bb9077cba948c64a1
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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