Sodium hydride → HCID 66704611, Verbindung

HRID 425080

Reaktionsgleichung

Reaktionsgleichung von HRID 425080
[O:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.[H-].[Na+].CC1C=CC(S(O[CH2:20][CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]3[CH:35]=[C:34]([Br:36])[CH:33]=[CH:32][C:31]=3[Cl:37])=[CH:25][CH:24]=2)(=O)=O)=CC=1>O1CCCC1>[Br:36][C:34]1[CH:33]=[CH:32][C:31]([Cl:37])=[C:30]([CH:35]=1)[CH2:29][C:26]1[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH2:20][O:6][C@H:3]2[CH2:4][CH2:5][O:1][CH2:2]2)=[CH:28][CH:27]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 641512(-)-3-HydroxytetrahydrofuranHCID 59557747HCID 59557747, Verbindung

Produkt 1

HCID 66704611HCID 66704611, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of (R)-tetrahydrofuran-3-ol (320 mg, 3.63 mmol) in dry tetrahydrofuran (10 mL) was added sodium hydride (145 mg, 3.63 mmol, 60%) slowly under 0° C. The reaction was stirred at this temperature for 30 min and then 2-(4-(5-bromo-2-chlorobenzyl)phenoxy)ethyl 4-methylbenzenesulfonate (intermediate AB) (300 mg, 0.61 mmol) was added. The reaction was warmed to room temperature and then heated to reflux overnight. The reaction was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated to a yellow oil. The crude oil was purified by flash chromatography to get 200 mg of colorless oil (80% yield).

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customThe reaction was quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to a yellow oil
  8. customThe crude oil was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-13d2b61fe8d64769908f235f01fb2284
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106021B2

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