Water → HCID 10134854, Verbindung

HRID 496041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 496041
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[OH:12][CH2:13][C@H:14]1[CH2:28][O:27][C:17]2[CH:18]=[CH:19][C:20]3[C:21](=[O:26])[CH:22]=[CH:23][O:24][C:25]=3[C:16]=2[O:15]1.O>N1C=CC=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:12][CH2:13][CH:14]2[CH2:28][O:27][C:17]3[CH:18]=[CH:19][C:20]4[C:21](=[O:26])[CH:22]=[CH:23][O:24][C:25]=4[C:16]=3[O:15]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 69744945HCID 69744945, Verbindung

Produkt 1

HCID 10134854HCID 10134854, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

p-Toluenesulfonyl chloride (0.60 g, 3.15 mmole) was added to solution of (2S)-2-(hydroxymethyl)-2,3-dihydro-7H-[1,4]dioxino[2,3-h]chromen-7-one (0.41 g, 1.75 mmole) in 50 mL of pyridine. The solution was stirred at room temperature overnight under nitrogen. Water was added to quench the excess tosyl chloride and the solvent was removed in vacuum and replaced with methylene chloride. The solution was washed with 2N aqueous HCl, with saturated aqueous sodium bicarbonate, and with saturated brine, and dried over magnesium sulfate. Filtration, evaporation in vacuum and column chromatography on silica gel with 3% methanol/methylene chloride as eluant gave 0.36 g (54%) of the (R)-enantiomer of the title compound as a yellow solid, m.p. 190-191° C.

Aufarbeitung

  1. customto quench the excess tosyl chloride
  2. customthe solvent was removed in vacuum
  3. washThe solution was washed with 2N aqueous HCl, with saturated aqueous sodium bicarbonate
  4. dry with materialwith saturated brine, and dried over magnesium sulfate
  5. filtrationFiltration, evaporation in vacuum and column chromatography on silica gel with 3% methanol/methylene chloride as eluant

Quellen und Nachweise

ORD-Eintrag
ord-c9551230475b4781b5365b025d89cb3f
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943178B2

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