Tetrahydrofuran → 4-(4-Chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid

HRID 734667노트

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HRID 734667 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([O:18]C)=[O:17])=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+]>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:13][C:12](=[O:14])[NH:11][C:10]([CH3:15])=[C:9]2[C:16]([OH:18])=[O:17])=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 2849828Methyl 4-(4-chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylate

생성물 1

HCID 534357904-(4-Chlorophenyl)-2-methyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylic acid수율 71%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

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온도
60 °C

실험 절차

The product from Step 1 (735 mg, 2.63 mmol, 1.00 equiv) was dissolved in 3/1 MeOH:THF (12 mL total). Following addition of 2.5N NaOH (3 mL), the reaction mixture was heated to 60° C. for 6 hours, then stirred at room temperature for an additional 16 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed again with 1N NaOH. The aqueous phases were combined and acidified to pH˜1 with 5N HCl, and extracted twice with ethyl acetate. The combined organic extracts were washed with satd. NaCl, dried over Na2SO4, and filtered. The filtrate was concentrated en vacuo and azeotroped several times with hexanes to afford 494 mg (71%) of the acid as an off-white solid. MS (ES+) m/e 266 [M+H]+.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed again with 1N NaOH
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic extracts were washed with satd
  5. dry with materialNaCl, dried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated en vacuo
  8. customazeotroped several times with hexanes

출처 및 근거

ORD 기록
ord-447b958a032d4bc6bf7cee889e795264
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592357B2

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