Nitrogen → HCID 22905873, Verbindung

HRID 1488573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488573
Br[C:2]1[CH:7]=[C:6](Br)[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[O:13][CH2:14][CH2:15]Br.N#N.C([Li])CCC.CCCCCC.[NH4+].[Cl-]>O1CCCC1.CCCCCC.CO.CCOCC>[C:9]([C:4]1[C:3]2[O:13][CH2:14][CH2:15][C:2]=2[CH:7]=[CH:6][CH:5]=1)([CH3:12])([CH3:11])[CH3:10]

Komponenten

8

Edukt 5

HCID 947NitrogenHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 22905874HCID 22905874, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 22905873HCID 22905873, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 21864698Diethyl ether methanolLösungsmittelHCID 21883165Tetrahydrofuran hexaneLösungsmittel

Versuchsvorschrift

A cold solution of 1,5-dibromo-2-(2-bromoethoxy)-3-tert-butylbenzene (5.00 g, 12.05 mmol) in tetrahydrofuran/hexane (100 mL/20 mL) is cooled to -95° C. (MeOH/Et2O, liquid N2). A solution of n-butyl lithium in hexane (12 mL, 30.1 mmol) is added dropwise, and the reaction is allowed to stir for 0.5 h between -95° C. and -80° C. After 4 h, the reaction is poured onto saturated NH4Cl, and extracted with ethylacetate. The organic layer is washed twice with H2O and once with brine. The combined organic layers are dried (MgSO4), filtered, and evaporated. The resulting oil is purified by chromatography over SiO2 using hexanes. The resulting oil is distilled at reduced pressure to give 7-tert-butyl-2,3-dihydrobenzo[b]furan as a low melting white solid.

Aufarbeitung

  1. waitAfter 4 h
  2. extractionextracted with ethylacetate
  3. washThe organic layer is washed twice with H2O and once with brine
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe resulting oil is purified by chromatography over SiO2
  8. distillationThe resulting oil is distilled at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2b97fe46743540aaabf64026ea4b5ea1
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05674891

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