Sodium methanethiolate → HCID 66609952, Verbindung

HRID 1404721

Reaktionsgleichung

Reaktionsgleichung von HRID 1404721
[CH3:1][S-:2].[Na+].CS(O[CH2:9][C:10]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:12][CH2:11]1)(=O)=O>CN(C)C=O.O>[CH3:1][S:2][CH2:9][C:10]1([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:12]1

Komponenten

5

Edukt 2

HCID 4378561Sodium methanethiolateHCID 574666101-Methanesulfonyloxymethyl-cyclopropanecarboxylic acid ethyl ester

Produkt 1

HCID 66609952HCID 66609952, VerbindungAusbeute 100,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

Sodium methanethiolate (700 mg, 9.9 mmol, 2.0 equiv) was added to a stirred solution of ethyl 1-((methylsulfonyloxy)methyl)cyclopropanecarboxylate (1.1 g, 4.9 mmol, 1.0 equiv) in N,N-dimethylformamide (10 mL) at 23° C. The resulting brown suspension was stirred at 23° C. for 18 h. The reaction mixture was diluted with water (500 mL) and extracted with diethyl ether (4×100 mL). The combined organic layers were dried (MgSO4), gravity-filtered, and concentrated by rotary evaporation to afford the title compound as a brown oil (860 mg, 99%): 1H NMR (300 MHz, CDCl3) δ 4.14 (q, J=7 Hz, 2H), 2.83 (s, 2H), 2.16 (s, 3H), 1.31 (dd, J=7, 4 Hz, 2H), 1.25 (t, J=7 Hz, 3H), 0.89 (dd, J=7, 4 Hz, 2H).

Aufarbeitung

  1. extractionextracted with diethyl ether (4×100 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-c4de1fda383a4bb0abff8927b105a221
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08912338B2

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