Ethyl Acetate → Ethyl 2-(cyclopropylmethoxy)acetate

HRID 518365

Reaktionsgleichung

Reaktionsgleichung von HRID 518365
[CH2:1]([O:3][C:4](=[O:8])[CH:5]=[N+]=[N-])[CH3:2].[CH:9]1([CH2:12][OH:13])[CH2:11][CH2:10]1.CC(=O)OCC>C(Cl)Cl>[CH:9]1([CH2:12][O:13][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:8])[CH2:11][CH2:10]1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 12192Ethyl diazoacetateHCID 75644Cyclopropanemethanol

Produkt 1

HCID 43119684Ethyl 2-(cyclopropylmethoxy)acetateAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Diazoacetic acid ethyl ester (80.00 g, 0.70 mol) was added dropwise to cyclopropanemethanol (60.66 g, 0.84 mol) and [Rh(Ac2O)2]2 (3.1 g, 7.02 mmol) in anhydrous CH2Cl2 (800 mL) at 0° C. The mixture was stirred at 0° C. for 30 min and at room temperature for 4 h. CH2Cl2 extractive work up and silica gel chromatography (PE: EA=100:1-50:1) gave the title compound (100 g, 90.4% yield) as a colorless oil. 1H NMR: (CDCl3, 400 MHz) δ 4.23-4.19 (m, 2H), 4.09 (s, 2H), 3.38-3.36 (m, 2H), 1.27 (t, J=7.2 Hz, 3H), 1.10-1.07 (m, 1H), 0.57-0.52 (m, 2H), 0.24-0.20 (m, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-aa54ae4b9540440da230611a37444f9c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115114B2

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