Diethyl Ether → Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate

HRID 255948

Reaktionsgleichung

Reaktionsgleichung von HRID 255948
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[C:6]([O:10][CH3:11])(=[O:9])C=C.[CH3:12][CH2:13]OCC>>[CH:2]12[CH2:1][CH:5]([CH:12]=[CH:13]1)[CH2:4][CH:3]2[C:6]([O:10][CH3:11])=[O:9]

Komponenten

4

Edukt 3

HCID 3283Diethyl EtherHCID 7294Methyl AcrylateHCID 7612Cyclopentadiene

Produkt 1

HCID 250075Methyl bicyclo[2.2.1]hept-5-ene-2-carboxylate

Versuchsvorschrift

In 100 ml of anhydrous ether at 0° C. is mixed 30 ml of cyclopentadiene and 32 ml of methyl acrylate. The ice bath is removed and the mixture allowed to stir overnight. The solvent, unreacted methyl acrylate, and cyclopentadiene are removed at ambient temperature at reduced pressure; as less material distilled out of the mixture the pressure is gradually reduced to 0.5 mm. The desired epimeric mixture of methyl carboxylates is distilled at 42°-43° and 0.5 mm; ir: 3118, 3060, 2965, 2941, 2862, 1734, 1428, 1329, 1264, 1190, 1024, 704, cm-1 ; 60 MHz NMR: endo/exo=80/20.

Aufarbeitung

  1. customThe ice bath is removed
  2. customThe solvent, unreacted methyl acrylate, and cyclopentadiene are removed at ambient temperature at reduced pressure
  3. distillationas less material distilled out of the mixture the pressure
  4. additionThe desired epimeric mixture of methyl carboxylates
  5. distillationis distilled at 42°-43°

Quellen und Nachweise

ORD-Eintrag
ord-1400422becca49a1bb6736325ef80823
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04699963

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