Hydrochloric Acid → HCID 178418644, Verbindung

HRID 5249

Reaktionsgleichung

Reaktionsgleichung von HRID 5249
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].C(N(CC)CC)C.[C:15](Cl)(=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[OH:3][C:2]1[CH2:4][O:5][C:6](=[O:7])[C:1]=1[C:15](=[O:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 521261Tetronic acid

Produkt 1

HCID 178418644HCID 178418644, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirring solution of 1.6 g (16 mmol) of tetronic acid in 75 mL of methylene chloride is added 2.5 mL (17.86 mmol) of triethylamine and 640 mg of 4-dimethylaminopyridine at 0° C. Next, 5.0 g (17.6 mmol) of stearoyl chloride is added and the reaction is stirred overnight at room temperature. The reaction is acidified with 1.0N HCl and extracted with two 100 mL portions of methylene chloride. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude compound. Pure material was obtained by trituration with ethyl acetate as affording 3.3 g (58%) of 4-hydroxy-3-(1-oxooctadecyl)-2(5H)-furanone.

Aufarbeitung

  1. extractionextracted with two 100 mL portions of methylene chloride
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customaffording crude compound

Quellen und Nachweise

ORD-Eintrag
ord-86ae5c67c1df403db2f7cf7d7103c33f
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05242945

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