Triethylamine → 6-(Methanesulfonyloxymethyl)quinoline

HRID 392507

Reaktionsgleichung

Reaktionsgleichung von HRID 392507
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl>[CH3:20][S:21]([O:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2)(=[O:23])=[O:22]

Komponenten

5

Edukt 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 15143856-Hydroxymethylquinoline

Produkt 1

HCID 226628996-(Methanesulfonyloxymethyl)quinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

6-Hydroxymethylquinoline (0.4325 g, 2.72 mmoles) (prepared by the method of: C. E. Kaslow and W. R. Clark, J. Org. Chem., 1953, 18, 55-58.) and triethylamine (1.5147 mL, 10.87 mmoles) were dissolved in anhydrous dichloromethane (16 mL) and the mixture was cooled to 0° C. Methanesulfonyl chloride (0.421 mL, 5.43 mmoles) was added and the mixture was stirred under argon at 0° C. for 1 h. Additional triethylamine (0.758 mL, 5.435 mmoles) and methanesulfonyl chloride (0.211 mL, 2.72 mmoles) were added and the reaction was allowed to proceed for a further 1 h at 0° C. The mixture was evaporated to dryness to give the title compound which was used without further purification in the next step.

Aufarbeitung

  1. waitto proceed for a further 1 h at 0° C
  2. customThe mixture was evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f712418d72d7419fa0925dc5983983d2
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06800636B2

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