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

HRID 734667ノート

反応式

HRID 734667 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-447b958a032d4bc6bf7cee889e795264
出典データセット
uspto-grants-2009_09
特許番号
US07592357B2

反応ノート

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