Pyridine → Trifluoromethanesulfonic acid cyclopentylmethyl ester

HRID 889591Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 889591
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH:16]1([CH2:21]O)[CH2:20][CH2:19][CH2:18][CH2:17]1.N1C=CC=CC=1>C(Cl)Cl>[CH:16]1([CH2:21][O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH2:20][CH2:19][CH2:18][CH2:17]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 77195Cyclopentanemethanol

Produkt 1

HCID 57617550Trifluoromethanesulfonic acid cyclopentylmethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-40 °C

Versuchsvorschrift

Trifluoromethanesulfonic anhydride (6.72 mL, 39.94 mmol) is dissolved in DCM (40 mL) and cooled to −40° C. To this is added dropwise cyclopentanemethanol (4.00 g, 39.94 mmol) dissolved in DCM (10 mL) and anhydrous pyridine (3.23 mL, 39.94 mmol). The reaction is stirred at −40° C. for 45 min. The reaction is diluted with hexanes (30 mL) and run through a plug of silica using hexanes (300 mL) as the eluent. Concentration without heating gives trifluoromethanesulfonic acid cyclopentylmethyl ester as a clear, colorless oil that is used immediately.

Aufarbeitung

  1. concentrationConcentration
  2. temperaturewithout heating

Quellen und Nachweise

ORD-Eintrag
ord-5990291ae6d64b08b0f669d68e990b56
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08252931B2

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