2-Pyrrolidone → 4-[2-(2-oxopyrrolidin-1-yl)ethoxy]benzoic acid

HRID 1264086ノート

反応式

HRID 1264086 の反応式
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[H-].[Na+].[Na].Br[CH2:11][CH2:12][O:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[CH:16][CH:15]=1>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:6]=[C:2]1[CH2:3][CH2:4][CH2:5][N:1]1[CH2:11][CH2:12][O:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 120252-Pyrrolidone2 回HCID 24758Sodium hydrideHCID 1898264Methyl 4-(2-bromoethoxy)benzoateHCID 5360545Sodium

生成物 1

HCID 64972354-[2-(2-oxopyrrolidin-1-yl)ethoxy]benzoic acid収率 46.4%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

2-Pyrrolidinone (0.859 mL, 11.3 mmol, 2.6 eq) was added to a suspension of sodium hydride (452 mg of 60% w/w, 11.3 mmol, 2.6 eq.) in THF (10 mL). After 1 h, the suspension of the sodium salt of 2-pyrrolidinone thus formed was added to a solution of methyl 4-(2-bromoethoxy)benzoate (1.17 g, 4.52 mmol) and a catalytic amount of tetrabutylammonium iodide in dry THF (10 mL). The reaction was heated at reflux for 18 h. The reaction mixture was concentrated under reduced pressure then the residue partitioned between ethyl acetate (150 mL) and 2 N sodium hydroxide (50 mL). The aqueous layer was made acidic to pH 3 with conc. HCl; then the solvent was removed under reduced pressure. The resulting solid was triturated with ethyl acetate to give the acid as a white solid (523 mg, 46%).

後処理

  1. customthus formed
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 18 h
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customthe residue partitioned between ethyl acetate (150 mL) and 2 N sodium hydroxide (50 mL)
  6. customthen the solvent was removed under reduced pressure
  7. customThe resulting solid was triturated with ethyl acetate

出典と根拠

ORDレコード
ord-27c4a2429e57477e91c93580fa16e99d
出典データセット
uspto-grants-2003_04
特許番号
US06541499B1

反応ノート

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