tert-Butanol → HCID 54493274, Verbindung

HRID 1779431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1779431
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.[C:25]1([S:31]([C:34]2[S:38]C(C(O)=O)=C[CH:35]=2)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:25]1([S:31]([C:34]2[S:38][C:6]([NH:3][C:4](=[O:15])[O:46][C:42]([CH3:45])([CH3:44])[CH3:43])=[CH:7][CH:35]=2)(=[O:32])=[O:33])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Komponenten

5

Edukt 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2202575-(Benzenesulfonyl)thiophene-2-carboxylic acid

Produkt 1

HCID 54493274HCID 54493274, Verbindung

Versuchsvorschrift

Triethylamine (0.62 ml, 4.4 mmol) and diphenylphosphoryl azide (0.97 ml, 4.5 mmol) are added to 5-(phenylsulfonyl)thiophene-2-carboxylic acid (1.00 g, 3.7 mmol) in 40 ml of absolute tert-butanol. The reaction mixture is boiled under reflux for 5 hours. The solvent is distilled off. The residue is taken up in ethyl acetate and washed with water. The organic phase is dried over magnesium sulfate and filtered and the solvent is distilled off. The green-black oil which remains is purified by flash chromatography (eluent: 33% v/v ethyl acetate in petroleum ether (40/60)).

Aufarbeitung

  1. temperatureunder reflux for 5 hours
  2. distillationThe solvent is distilled off
  3. washwashed with water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. distillationthe solvent is distilled off
  7. customThe green-black oil which remains is purified by flash chromatography (eluent: 33% v/v ethyl acetate in petroleum ether (40/60))

Quellen und Nachweise

ORD-Eintrag
ord-1a12e22b73b24525b9999861d79ae096
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05627198

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