Dimethylformamide → HCID 59093767, Verbindung

HRID 1167603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1167603
[Li+].CC([N-]C(C)C)C.[CH2:9]1[CH2:13][O:12][CH2:11][CH2:10]1.[Se:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19]1[Se:20][C:21]([C:24]2[Se:25]C=CC=2)=[CH:22][CH:23]=1.CN(C=O)C>C(OCC)(=O)C>[CH:11]([C:10]1[Se:25][C:24]([C:21]2[Se:20][C:19]([C:15]3[Se:14][CH:18]=[CH:17][CH:16]=3)=[CH:23][CH:22]=2)=[CH:13][CH:9]=1)=[O:12]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 599441801~2~,2~2~:2~5~,3~2~-Terselenophene

Produkt 1

HCID 59093767HCID 59093767, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

LDA (1.0 M solution in THF, 310 mL) was added to an anhydrous THF solution (4 mL) containing 2,2′:5′,2″-terselenophene (100 mg) under N2 at −78° C. The solution was stirred at −78° C. for 3 h, anhydrous DMF (1 mL) was added, stirred at −78° C. for 1 h, and slowly warmed to room temperature. The reaction solution was diluted with ethyl acetate (100 mL) and washed with H2O (4×100 mL). The organic layer was separated, dried over MgSO4, filtered, and the solvent was removed under vacuum. The residue was chromatographed over silica gel using CH2Cl2 to afford 2-formyl-5,2′:5′,2″-terselenophene in 75% yield.

Aufarbeitung

  1. stirringstirred at −78° C. for 1 h
  2. temperatureslowly warmed to room temperature
  3. washwashed with H2O (4×100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed under vacuum
  8. customThe residue was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6862255bc0d94004a9622407dbe94e2b
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620804B2

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