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Hydrochloric Acid → HCID 86584292, Verbindung

HRID 1415874
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1415874
[C:1]([O:16][CH:17]([CH2:20][O:21][C:22](=[O:36])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:18][OH:19])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:37]1([CH3:47])[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1.Cl>N1C=CC=CC=1>[C:1]([O:16][CH:17]([CH2:20][O:21][C:22](=[O:36])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:18][OH:19])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[S:43]([C:40]1[CH:41]=[CH:42][C:37]([CH3:47])=[CH:38][CH:39]=1)([O-:15])(=[O:45])=[O:44]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 89298Glyceryl Dimyristate

Produkt 1

HCID 86584292HCID 86584292, VerbindungAusbeute 131,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2,3 Dimyristoylglycerol (600 mg, 1.4 mmol) was dissolved in pyridine and the solution cooled to 0° C. The solution was stirred under a nitrogen atmosphere and p-toluenesulfonyl chloride (300 mg, 1.57 mmol) was added. The solution was allowed to warm to room temperature and was then stirred overnight at ambient temperature. To the solution was added hydrochloric acid (2.5M, 20 mL) and the solution was extracted three times with methylene chloride (25 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to give a crude oil. The oil was purified by flash chromatography (50 g of silica gel, 60 Å) eluting with 5% ethyl acetate/hexane. The oil obtained by flash chromatography was dried under high vacuum at ambient temperature to give 2,3-Dimyristoylglycerol-tosylate (630 mg, 77% yield).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringwas then stirred overnight at ambient temperature
  3. extractionthe solution was extracted three times with methylene chloride (25 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude oil
  8. customThe oil was purified by flash chromatography (50 g of silica gel, 60 Å)
  9. washeluting with 5% ethyl acetate/hexane
  10. customThe oil obtained by flash chromatography
  11. customwas dried under high vacuum at ambient temperature

Quellen und Nachweise

ORD-Eintrag
ord-745fdd2caad34296b886e2762878c7b8
Quelldatensatz
uspto-grants-1999_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05910487

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