Hydrochloric Acid → 2-(4-Nitro-benzyl)-5-(4-nitro-phenyl)-3-oxo-pentanoic acid ethyl ester

HRID 1003830Notes

Reaction equation

HRID 1003830 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6](=[O:18])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)[CH3:2].[H-].[Na+].[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([O-:24])=[O:23].Cl>C1COCC1>[CH2:1]([O:3][C:4](=[O:19])[CH:5]([CH2:29][C:28]1[CH:31]=[CH:32][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=1)[C:6](=[O:18])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 660114-Nitrobenzyl bromideHCID 235003915-(4-Nitro-phenyl)-3-oxo-pentanoic acid ethyl ester

Product 1

HCID 543227172-(4-Nitro-benzyl)-5-(4-nitro-phenyl)-3-oxo-pentanoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4-nitro-phenyl)-3-oxo-pentanoic acid ethyl ester prepared in Example FF (14.2 g, 54 mmol) in dry THF (150 mL) was added NaH (2.43 g of a 60% dispersion in oil, 57.5 mmol), and the mixture was stirred at room temperature for 45 minutes. 4-Nitrobenzyl bromide (13.9 g, 64.3 mmol) was added all at once, and the resulting suspension was stirred overnight at room temperature. Dilute HCl (2N, 100 mL) was added. The solution was extracted with EtOAc; the extracts were combined, washed with brine, and dried (MgSO4). Concentration gave a residue which was chromatographed on silica gel, eluting with 5:1 hexane:EtOAc to 1:1 hexane:EtOAc, to yield the title compound. 1H NMR (CDCl3) δ 1.11 (t, 3 H), 2.66 (m, 1 H), 2.95 (m, 3 H), 3.21 (m, 2 H), 3.75 (t, 1 H), 4.07 (m, 2 H), 7.23 (m, 4 H), 8.05 (d, 4 H).

Workup

  1. stirringwas stirred overnight at room temperature
  2. extractionThe solution was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationConcentration
  6. customgave a residue which
  7. customwas chromatographed on silica gel
  8. washeluting with 5:1 hexane

Sources & evidence

ORD record
ord-0db3dad7e67848f7858d9c3328590dc1
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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