Water → HCID 58248246, Verbindung

HRID 874386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 874386
[O:1]1[CH2:5][CH2:4][C@@H:3]([OH:6])[CH2:2]1.C(N(CC)CC)C.[CH3:14][S:15](Cl)(=[O:17])=[O:16].O>C(Cl)Cl>[CH3:14][S:15]([O:6][C@@H:3]1[CH2:4][CH2:5][O:1][CH2:2]1)(=[O:17])=[O:16]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 641512(-)-3-Hydroxytetrahydrofuran

Produkt 1

HCID 58248246HCID 58248246, VerbindungAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of (R)-tetrahydrofuran-3-ol (1.1 g, 12.5 mmol) and triethylamine (13.6 mL, 97.5 mmol) in CH2Cl2 was cooled in an ice-water bath. To this, methanesulfonyl chloride (3.0 mL, 39 mmol) diluted in CH2Cl2 (10 mL) was added dropwise. The reaction was left stirring for 12 hours at room temperature. Water was added, and organic phases extracted in CH2Cl2 (3×50 mL), which were subsequently dried onto silica and purified by silica gel chromatography (50% EtOAc:Hexanes to 100% EtOAc gradient) to afford (R)-tetrahydrofuran-3-yl methanesulfonate (0.97 g, brown oil, 47% yield).

Aufarbeitung

  1. additionwas added dropwise
  2. waitThe reaction was left
  3. extractionorganic phases extracted in CH2Cl2 (3×50 mL)
  4. customwhich were subsequently dried onto silica
  5. custompurified by silica gel chromatography (50% EtOAc:Hexanes to 100% EtOAc gradient)

Quellen und Nachweise

ORD-Eintrag
ord-2e6f8caf5b2149f5858f92fc5dc1bf04
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980899B2

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