Triethylamine → 1-Methanesulfonyloxymethyl-cyclopropanecarboxylic acid ethyl ester

HRID 1404720

Reaktionsgleichung

Reaktionsgleichung von HRID 1404720
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][CH2:14][C:15]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16]1>ClCCl.O>[CH3:8][S:9]([O:13][CH2:14][C:15]1([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:17][CH2:16]1)(=[O:11])=[O:10]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 12450336Ethyl 1-(hydroxymethyl)cyclopropane-1-carboxylate

Produkt 1

HCID 574666101-Methanesulfonyloxymethyl-cyclopropanecarboxylic acid ethyl esterAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

Triethylamine (990 μL, 7.1 mmol, 1.2 equiv) and methanesulfonyl chloride (500 μL, 6.5 mmol, 1.1 equiv) were sequentially added to a stirred solution of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate (840 mg, 5.7 mmol, 1.0 equiv) in dichloromethane (15 mL) at 23° C. The resulting bright yellow solution was stirred at 23° C. for 20 h. The reaction mixture was diluted with water (100 mL) and extracted with dichloromethane (3×50 mL). The combined organic layers were dried (MgSO4), gravity-filtered, and concentrated by rotary evaporation to afford the title compound as a brown oil (1.1 g, 85%): 1H NMR (300 MHz, CDCl3) δ 4.33 (s, 2H), 4.16 (q, J=7 Hz, 2H), 3.08 (s, 3H), 1.43 (dd, J=7, 4 Hz, 2H), 1.26 (t, J=7 Hz, 3H), 1.04 (dd, J=7, 4 Hz, 2H).

Aufarbeitung

  1. extractionextracted with dichloromethane (3×50 mL)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationgravity-filtered
  4. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-36420efecc224bdbac64f3eed8b32be4
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912338B2

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