Ethyl Acrylate → 1,2-Diethyl (1R,2R)-1,2-cyclopropanedicarboxylate

HRID 271984

Reaktionsgleichung

Reaktionsgleichung von HRID 271984
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].[CH2:8]([O:10][C:11]([CH2:13][S+](C)C)=[O:12])[CH3:9]>C(Cl)(Cl)Cl>[CH2:8]([O:10][C:11]([C@@H:13]1[CH2:3][C@H:2]1[C:1]([O:5][CH2:6][CH3:7])=[O:4])=[O:12])[CH3:9]

Komponenten

4

Edukt 2

HCID 8821Ethyl AcrylateHCID 78862(Ethoxycarbonylmethyl)dimethylsulfonium

Produkt 1

HCID 117153031,2-Diethyl (1R,2R)-1,2-cyclopropanedicarboxylateAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

Ethyl acrylate (99%, 270 g, 1.4 eq.) was added to a solution of 2 (282 g, 1.91 mol) in CHCl3 (1500 mL) at 5° C. Cooling was removed and the reaction was stirred at 22° C. for 12 h. Evaporation of the solvent and excess acrylate left an orange oil, which was vacuum distilled (bp 70-75° C./1 mm) to produce 3 (286 g, 80.6%) as a clear thick oil. 1H NMR (250 MHz, CDCl3) δ4.15 (q, J=7.1, 4H); 2.16 (dd, J=7.5, 5.7, 2H); 1.41 (dd, J=7.5, 5.7, 2H); 0.88 (t, J=7.1, 6H). 13C NMR (62.5 MHz, CDCl3) δ 171.69; 60.96; 22.26; 15.18; 14.08.

Aufarbeitung

  1. temperatureCooling
  2. customwas removed
  3. customEvaporation of the solvent and excess acrylate
  4. waitleft an orange oil, which
  5. distillationdistilled (bp 70-75° C./1 mm)

Quellen und Nachweise

ORD-Eintrag
ord-78911f11bfef430cba31346b439c2e24
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07453011B2

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