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

HRID 1353059

Reaction equation

HRID 1353059 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e055248d058841af828214408c0156d1
Source dataset
uspto-grants-2007_05
Patent number
US07220777B2

Linked notes

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