Sodium hydride → Ethyl[2Z]-2-methyl-3-[1-phenylpyrrol-2-yl]prop-2-enoate

HRID 1278956

Reaktionsgleichung

Reaktionsgleichung von HRID 1278956
[CH3:1][CH2:2][O:3][C:4]([CH:6](P(OCC)(OCC)=O)[CH3:7])=[O:5].[H-].[Na+].[C:18]1([N:24]2[CH:28]=[CH:27][CH:26]=[C:25]2[CH:29]=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH4+].[Cl-]>C1COCC1>[CH3:7]/[C:6](=[CH:29]/[C:25]1[N:24]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:28]=[CH:27][CH:26]=1)/[C:4]([O:3][CH2:2][CH3:1])=[O:5]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 107155Triethyl 2-phosphonopropionateHCID 9347291-phenyl-1H-pyrrole-2-carbaldehyde

Produkt 1

HCID 18431815Ethyl[2Z]-2-methyl-3-[1-phenylpyrrol-2-yl]prop-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Triethyl 2-phosphonopropionate (0.714 mol, 153 ml) was dissolved in THF (75 ml) and added slowly to NaH (1.0 mol, 24.3 g) in THF (60 ml) at 0° C. The mixture was slowly warmed to room temperature and stirring was continued for 1 h after gas evolution had ceased. The temperature was lowered to −10° C. and a solution of the above described 1-Phenylpyrrole-2-carbaldehyde (0.665 mol, 113.0 g) in 200 ml of THF was added dropwise. The flask and contents were warmed to room temperature over a 30 minute period resulting in a thick precipitate which decoupled the magnetic stirrer. A saturated solution of NH4Cl (100 ml) was added cautiously dissolving the precipitate to give a two phase solution. After evaporating the THF, the crude product was extracted with ether (2×200 ml). The extract was washed with brine solution, dried over MgSO4, and solvents were removed on a rotoevaporator. Yield: 178 g of product as a white solid (98%). The title compound was analysed by 1H-NMR and 13C-NMR spectroscopy.

Aufarbeitung

  1. customwas lowered to −10° C.
  2. additionwas added dropwise
  3. temperatureThe flask and contents were warmed to room temperature over a 30 minute period
  4. customresulting in a thick precipitate which
  5. dissolutiondissolving the precipitate
  6. customto give a two phase solution
  7. customAfter evaporating the THF
  8. extractionthe crude product was extracted with ether (2×200 ml)
  9. washThe extract was washed with brine solution
  10. dry with materialdried over MgSO4, and solvents
  11. customwere removed on a rotoevaporator

Quellen und Nachweise

ORD-Eintrag
ord-1a583b067fb947098b36095337f5657d
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06444833B1

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