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Diethyl Ether → (2S,5S)-2-(4'-octyloxycarbonylbenzyloxy)-5-hexyl-delta-valerolactone

HRID 893253
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 893253
Br[CH2:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:8])=[CH:5][CH:4]=1.[OH:20][C@H:21]1[CH2:27][CH2:26][C@@H:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[O:24][C:22]1=[O:23].C(OCC)C>CN(C)C=O.[Ag]=O>[CH2:10]([O:9][C:7]([C:6]1[CH:18]=[CH:19][C:3]([CH2:2][O:20][C@H:21]2[CH2:27][CH2:26][C@H:25]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[O:24][C:22]2=[O:23])=[CH:4][CH:5]=1)=[O:8])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 14645393(2S,5R)-hydroxy-5-hexyl-delta-valerolactoneHCID 19891718Octyl p-bromomethylbenzoate

Produkt 1

HCID 22844672(2S,5S)-2-(4'-octyloxycarbonylbenzyloxy)-5-hexyl-delta-valerolactoneAusbeute 2,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 92152Silver(II) oxide
Katalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In 1.5 ml of dry dimethylformamide were dissolved 180 mg of octyl p-bromomethylbenzoate and 100 mg of (2S,5R)-2-hydroxy-5-hexyl-δ-valerolactone, and 300 mg of silver oxide was added to the solution and the mixture was stirred overnight at room temperature to effect reaction. After the reaction, diethyl ether was added to the reacted solution to extract the reaction product. The extract was washed with a saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate. Diethyl ether was removed by distillation under a reduced pressure. The obtained crude product was purified by the silica gel column chromatography to obtain 5 mg of (2S,5S)-2-(4'-octyloxycarbonylbenzyloxy)-5-hexyl-δ-valerolactone.

Aufarbeitung

  1. additionwas added to the solution
  2. customreaction
  3. additionwas added to the reacted solution
  4. extractionto extract the reaction product
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried on anhydrous magnesium sulfate
  7. customDiethyl ether was removed by distillation under a reduced pressure
  8. customThe obtained crude product
  9. customwas purified by the silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-b48a4ea2f39144efb591a471b81abbd8
Quelldatensatz
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05124069

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