Water → (S)-tetrahydrofuran-3-yl methanesulfonate

HRID 2365766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2365766
[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 2733227(S)-(+)-3-Hydroxytetrahydrofuran

Produkt 1

HCID 57561588(S)-tetrahydrofuran-3-yl methanesulfonateAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of (S)-tetrahydrofuran-3-ol (1.0 g, 11 mmol) and triethylamine (9.4 mL, 86 mmol) in CH2Cl2 (20 mL) 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 (S)-tetrahydrofuran-3-yl methanesulfonate (1.52 g, brown oil, 83% 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-1e0320a797c94a76abaeab62da60a7f5
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697709B2

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