Sodium hydride → 1-(2-(2-Methoxy-4-nitrophenoxy)ethyl)pyrrolidine

HRID 1353059

反応式

HRID 1353059 の反応式
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.[H-].[Na+].Cl[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][C:13]=1[O:21][CH3:22]>CN(C)C=O>[CH3:22][O:21][C:13]1[CH:14]=[C:15]([N+:18]([O-:20])=[O:19])[CH:16]=[CH:17][C:12]=1[O:1][CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 705192-Chloro-5-nitroanisoleHCID 762881-Pyrrolidineethanol

生成物 1

HCID 179893551-(2-(2-Methoxy-4-nitrophenoxy)ethyl)pyrrolidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of the 1-(2-hydroxyethyl)-pyrrolidine [Aldrich], (1.87 ml, 16 mmol) in dimethylformamide was added portionwise sodium hydride [60% dispersion in oil, (544 mg, 16 mmol). After stirring at room temperature for 10 minutes a solution of 1-chloro-2-methoxy-4-nitro-benzene [Avocado] (3 g, 16 mmol) in dimethylformamide (10 ml) was added dropwise. The reaction mixture was left stirring at room temperature for 16 hrs then concentrated. The residue was dissolved in ethyl acetate (200 ml) and washed with water (3×50 ml). The organic phase was dried with magnesium sulphate, evaporated and the residue purified by flash chromatography on silica gel using dichloromethane-aq. ammonia-methanol as eluent to afford 1-[2-(2-methoxy-4-nitro-phenoxy)-ethyl]-pyrrolidine as a brown oil.

後処理

  1. additionwas added dropwise
  2. waitThe reaction mixture was left
  3. concentrationthen concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate (200 ml)
  5. washwashed with water (3×50 ml)
  6. dry with materialThe organic phase was dried with magnesium sulphate
  7. customevaporated
  8. customthe residue purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-e055248d058841af828214408c0156d1
出典データセット
uspto-grants-2007_05
特許番号
US07220777B2

関連ノート

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