Triethylamine → 1-Methanesulfonyloxymethyl-cyclopropanecarboxylic acid ethyl ester

HRID 1428368

Reaktionsgleichung

Reaktionsgleichung von HRID 1428368
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 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

Triethylamine (5.57 mL, 40.00 mmol) and methanesulfonyl chloride (2.85 mL, 36.60 mmol) were sequentially added to a stirred solution of ethyl 1-(hydroxymethyl)cyclopropanecarboxylate (4.80 g, 33.30 mmol) in dichloromethane (83 mL) at 23° C. The resulting bright yellow solution was stirred at 23° C. for 20 h. The reaction mixture was diluted with water and extracted with dichloromethane. The combined organic layers were dried (MgSO4), filtered, and concentrated to dryness to give the desired product as a brown oil (6.92 g, 94%): 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
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-95d3ba03b4304c349d5c61f0598d0543
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937083B2

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