m-Chloroperbenzoic acid → 1,5:2,3-Dianhydro-3-C-(3-bromophenyl)-4-deoxypentitol

HRID 1842156Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1842156
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:14]=[C:15]([C:19]2[CH2:20][CH2:21][O:22][CH2:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([C:19]23[O:9][CH:20]2[CH2:21][O:22][CH2:23][CH2:24]3)[CH:16]=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57475766HCID 57475766, Verbindung

Produkt 1

HCID 578277501,5:2,3-Dianhydro-3-C-(3-bromophenyl)-4-deoxypentitolAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-Chloroperbenzoic acid (purity: 80%, 25.1 g) was added to a solution of 4-(3-bromophenyl)-3,6-dihydro-2H-pyran (21.4 g) in dichloromethane (400 mL) in an ice bath. The mixture was stirred at the same temperature for three hours, and then warmed to room temperature and stirred for five hours. Ice and a saturated sodium bicarbonate solution were added to the reaction mixture, and the organic layer was separated. The organic layer was sequentially washed with a saturated sodium bicarbonate solution, a sodium thiosulfate solution and brine. The aqueous layers were combined and extracted with ethyl acetate, and the organic layer was sequentially washed with a sodium bicarbonate solution, a sodium thiosulfate solution and brine. The organic layers were combined and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (17.5 g).

Aufarbeitung

  1. stirringstirred for five hours
  2. customthe organic layer was separated
  3. washThe organic layer was sequentially washed with a saturated sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was sequentially washed with a sodium bicarbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5095fbc72ed84f63afdc0c532de4a335
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946211B2

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