Dimethylformamide → 2-Cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid ethyl ester

HRID 502883Notes

Reaction equation

HRID 502883 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH:5]([C:10]#[N:11])[CH2:6][CH2:7][CH:8]=[CH2:9])[CH3:2].CN(C=O)C.[H-].[Na+].Cl[CH2:21][C:22]1[CH:27]=[C:26]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]=[CH:24][C:23]=1[N+:35]([O-:37])=[O:36]>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]([C:10]#[N:11])([CH2:21][C:22]1[CH:27]=[C:26]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:25]=[CH:24][C:23]=1[N+:35]([O-:37])=[O:36])[CH2:6][CH2:7][CH:8]=[CH2:9])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 249735162-Cyano-hex-5-enoic acid ethyl esterHCID 574757162-Chloromethyl-1-nitro-4-phenoxy-benzene

Product 1

HCID 574757172-Cyano-2-(2-nitro-5-phenoxy-benzyl)-hex-5-enoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a round bottom flask equipped with a nitrogen inlet 2-cyano-hex-5-enoic acid ethyl ester (2.0 g, 11.96 mmol) and DMF (40 mL) were added. The reaction mixture was cooled to 0° C. followed by addition of NaH (0.48 g, 12.0 mmol, 60% dispersion in mineral oil). The reaction mixture was allowed to stir at 0° C. for another 5 min, followed by addition of 2-chloromethyl-1-nitro-4-phenoxy-benzene (2.6 g, 9.86 mmol). The reaction turned a dark purple color. After 3 h the reaction was quenched with 1N HCl, and the solvent was evaporated to yield crude mixture. The crude mixture was dissolved in ethyl acetate and washed 3 times with 1N HCl followed by a wash with saturated brine solution. The phases were separated, and the organic phase was dried with sodium sulfate and filtered, and the solvent was removed under reduced pressure to yield a residue. The residue was purified by flash chromatography using heptanes/ethyl acetate as the mobile phase 9:1 to yield a residue.

Workup

  1. additionwere added
  2. customAfter 3 h the reaction was quenched with 1N HCl
  3. customthe solvent was evaporated
  4. customto yield crude mixture
  5. washwashed 3 times with 1N HCl
  6. washa wash with saturated brine solution
  7. customThe phases were separated
  8. dry with materialthe organic phase was dried with sodium sulfate
  9. filtrationfiltered
  10. customthe solvent was removed under reduced pressure
  11. customto yield a residue
  12. customThe residue was purified by flash chromatography
  13. customto yield a residue

Sources & evidence

ORD record
ord-cd75e8ab031c4806ae4cea2f8a95370c
Source dataset
uspto-grants-2010_08
Patent number
US07776882B2

Reaction notes

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