Tetrahydrofuran → HCID 86591629, Verbindung

HRID 495460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 495460
[H-].[Na+].[CH3:3][CH2:4][O:5][C:6](/[CH:8]=[CH:9]/[CH2:10]P(OCC)(OCC)=O)=[O:7].[N+:19]([C:22]1[C:29](OC)=[C:28]([O:32][CH3:33])[CH:27]=[CH:26][C:23]=1[CH:24]=O)([O-:21])=[O:20].[NH4+].[Cl-].C1C[O:39][CH2:38]C1>O>[CH2:4]([O:5][C:6](=[O:7])[CH:8]=[CH:9][CH:10]=[CH:24][C:23]1[CH:26]=[C:27]([O:39][CH3:38])[C:28]([O:32][CH3:33])=[CH:29][C:22]=1[N+:19]([O-:21])=[O:20])[CH3:3]

Komponenten

7

Edukt 5

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1524373,4-Dimethoxy-2-nitrobenzaldehydeHCID 5365783Triethyl 4-phosphonocrotonate, mixture of isomers

Produkt 1

HCID 86591629HCID 86591629, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of NaH (0.24 g, 6.0 mmol) in THF (30 mL) at 0° C. was added a solution of triethyl 4-phosphonocrotonate (1.0 g, 4.0 mmol) in THF (5 mL) dropwise. The solution was warmed to RT and stirred for 1 h. Nitroveratraldehyde (0.844 g, 4.0 mmol) was added to the mixture in one portion and the reaction was stirred for an additional 30 min at RT. NH4Cl (aq., sat., 3 mL) was added slowly to quench the reaction, followed by H2O (30 mL). The THF solvent was removed under reduced pressure and the resulting mixture was extracted with EtOAc (3×10 mL). The organic extracts were combined, washed with brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure and the mixture was purified by chromatography on silica gel to afford the title compound.

Aufarbeitung

  1. stirringthe reaction was stirred for an additional 30 min at RT
  2. customto quench
  3. customthe reaction
  4. customThe THF solvent was removed under reduced pressure
  5. extractionthe resulting mixture was extracted with EtOAc (3×10 mL)
  6. washwashed with brine
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customthe mixture was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e4c766c5234f499c9a39221c5686675d
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06939874B2

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