Triethylamine → HCID 18367229, Verbindung

HRID 380117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380117
O[CH:2]([C:7]1[O:8][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1)[CH2:3][CH2:4][CH2:5]O.CS(Cl)(=O)=O.C([N:31]([CH2:34][CH3:35])CC)C>O1CCCC1.C(OCC)(=O)C>[CH2:34]([N:31]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:7]1[O:8][C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:11]=1)[C:35]1[CH:5]=[CH:4][CH:3]=[CH:2][CH:7]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18367433HCID 18367433, Verbindung

Produkt 1

HCID 18367229HCID 18367229, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-(1,4-dihydroxybutyl)-4,5-diphenyloxazole (1 g) in tetrahydrofuran (10 ml) were added methanesulfonyl chloride (1.6 g) and triethylamine (1.5 ml) at 0° C. The solution was diluted with ethyl acetate and washed with sat. NaHCO3 and brine, dried over MgSO4, and evaporated. The residue was dissolved in benzylamine (10 ml). After being stirred for 2 hours at 80° C., the mixture was partitioned between ether and water. The or-ganic layer was washed with water and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to afford 1-benzyl-2-(4,5-diphenyloxazol-2-yl)pyrrolidine (1.3 g).

Aufarbeitung

  1. washwashed with sat. NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. dissolutionThe residue was dissolved in benzylamine (10 ml)
  5. customthe mixture was partitioned between ether and water
  6. washThe or-ganic layer was washed with water and brine
  7. customThe dried solvent was evaporated in vacuo
  8. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6fe6ab96180f468e9c8ae339092dbe6e
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300344B1

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