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Benzoyl Peroxide → (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[5-(bromomethyl)-2-ethoxyphenyl]-D-glucitol

HRID 1375969
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1375969
[Br:1]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[C:27]([O:30][C@@H:31]1[C@@H:36]([O:37][C:38](=[O:40])[CH3:39])[C@H:35]([O:41][C:42](=[O:44])[CH3:43])[C@@H:34]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[O:33][C@H:32]1[C:50]1[CH:55]=[C:54]([CH3:56])[CH:53]=[CH:52][C:51]=1[O:57][CH2:58][CH3:59])(=[O:29])[CH3:28]>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[C:27]([O:30][C@@H:31]1[C@@H:36]([O:37][C:38](=[O:40])[CH3:39])[C@H:35]([O:41][C:42](=[O:44])[CH3:43])[C@@H:34]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[O:33][C@H:32]1[C:50]1[CH:55]=[C:54]([CH2:56][Br:1])[CH:53]=[CH:52][C:51]=1[O:57][CH2:58][CH3:59])(=[O:29])[CH3:28]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 58786152(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-(2-ethoxy-5-methylphenyl)-D-glucitol

Produkt 1

HCID 58786161(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[5-(bromomethyl)-2-ethoxyphenyl]-D-glucitolAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5943
Carbon Tetrachloride
Lösungsmittel
HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

N-bromosuccinimide (1.7 g) and benzoyl peroxide (0.1 g) were added to a solution of (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-(2-ethoxy-5-methylphenyl)-D-glucitol (3.7 g) in carbon tetrachloride (30.0 ml) and the mixture was refluxed with heating for one hour. The reaction mixture was diluted with chloroform and the diluted product was washed with saturated aqueous solution of sodium hydrogencarbonate, saturated aqueous solution of sodium thiosulfate, and saturated brine in that order and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The resulting precipitates were collected by filtration to obtain (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[5-(bromomethyl)-2-ethoxyphenyl]-D-glucitol (1.4 g).

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for one hour
  3. washthe diluted product was washed with saturated aqueous solution of sodium hydrogencarbonate, saturated aqueous solution of sodium thiosulfate, and saturated brine in that order
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customThe resulting precipitates
  8. filtrationwere collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-72b32baac77549a68697199466f8ae00
Quelldatensatz
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07169761B2

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