Sodium hydride → (2,4-Difluoro-5-nitrophenyl) 1-pyrrolidinecarboxylate

HRID 981863Notes

Reaction equation

HRID 981863 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([N+:11]([O-:13])=[O:12])=[CH:6][C:5]=1[OH:14].[N:15]1([C:20](Cl)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]1>O1CCCC1.C(OCC)(=O)C>[N:15]1([C:20]([O:14][C:5]2[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]([F:10])=[CH:9][C:4]=2[F:3])=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 709371-Pyrrolidinecarbonyl chlorideHCID 109210242,4-Difluoro-5-nitrophenol

Product 1

HCID 53894956(2,4-Difluoro-5-nitrophenyl) 1-pyrrolidinecarboxylateYield 67.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred, cold (0° C.) mixture of 1.74 g of sodium hydride (0.072 mole, 2.9 g of a 60% oil suspension) and 7.0 g (0.039 mole) of 2,4-difluoro-5-nitrophenol in 100 mL of tetrahydrofuran was added 6.4 g (0.048 mole) of 1-pyrrolidinecarbonyl chloride. The reaction mixture was allowed to warm to room temperature and was stirred for four hours. The mixture was diluted with ethyl acetate and was washed with an aqueous 10% hydrochloric acid solution. The organic phase was dried over anhydrous magnesium sulfate, filtered and filtrate evaporated under reduced pressure leaving a semi-solid residue. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate:n-heptane (50:50) to yield 7.2 g of (2,4-difluoro-5-nitrophenyl) 1-pyrrolidinecarboxylate. The nmr and ir spectra were consistent with the proposed structure.

Workup

  1. washwas washed with an aqueous 10% hydrochloric acid solution
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customfiltrate evaporated under reduced pressure
  5. customleaving a semi-solid residue
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with ethyl acetate:n-heptane (50:50)

Sources & evidence

ORD record
ord-b343def531704720a1e1d21ed73ec994
Source dataset
uspto-grants-1991_02
Patent number
US04994104

Reaction notes

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