Water → 2-Thienylmethyl methanesulfonate

HRID 52184

Reaktionsgleichung

Reaktionsgleichung von HRID 52184
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][OH:7].C(N(CC)CC)C.[CH3:15][S:16](Cl)(=[O:18])=[O:17].O>C(Cl)Cl>[CH3:15][S:16]([O:7][CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)(=[O:18])=[O:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 694672-Thiophenemethanol

Produkt 1

HCID 189734302-Thienylmethyl methanesulfonateAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a 0° C. mixture of 2-thiophenemethanol (2.80 g, 24.5 mmol) and triethylamine (5.10 mL, 36.8 mmol) in CH2Cl2 (25 mL) was added methanesulfonyl chloride (2.09 mL, 27.0 mmol) and the reaction mixture was stirred for 2 hours. The reaction mixture was poured into H2O and the layers were separated. The organic phase was washed with cold 1N HCl (3×), saturated aqueous NaHCO3, and brine, dried over MgSO4, filtered. and concentrated in vacuo. 2-thienylmethyl methanesulfonate (1.78 g, 38%) was obtained by chromatography on silica gel (20% ethyl acetate/hexane).

Aufarbeitung

  1. customthe layers were separated
  2. washThe organic phase was washed with cold 1N HCl (3×), saturated aqueous NaHCO3, and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationand concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7a6e7ff6416e4d33a0570bba9e53735b
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616596

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