Dabco → Ethyl 5-cyclopropylisoxazole-3-carboxylate

HRID 1918518

Reaktionsgleichung

Reaktionsgleichung von HRID 1918518
[C:1]([CH:3]1[CH2:5][CH2:4]1)#[CH:2].[N+:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([O-])=[O:7].C1N2CCN(CC2)C1>C(O)C>[CH:3]1([C:1]2[O:7][N:6]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:2]=2)[CH2:5][CH2:4]1

Komponenten

5

Edukt 3

HCID 9237DabcoHCID 69379Ethyl nitroacetateHCID 138823Cyclopropylacetylene

Produkt 1

HCID 55251041Ethyl 5-cyclopropylisoxazole-3-carboxylateAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethynylcyclopropane (0.40 mL; 4.58 mmol), ethyl 2-nitroacetate (1.30 mL; 11.46 mmol), and 1,4-diazobicyclo[2.2.2]octane (DABCO, 0.053 g; 0.458 mmol) in ethanol (3 mL) was irradiated in a microwave oven at 150° C. for 20 min and was then evaporated. The residue was dissolved in ethyl acetate and the solution was washed with water. The organic layer was evaporated and the residue was purified by flash chromatography on silica gel (eluent: 20 to 100% of dichloromethane in heptane) to afford 0.765 g (92%) of ethyl 5-cyclopropylisoxazole-3-carboxylate as a yellow oil.

Aufarbeitung

  1. customwas then evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed with water
  4. customThe organic layer was evaporated
  5. customthe residue was purified by flash chromatography on silica gel (eluent: 20 to 100% of dichloromethane in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-de869c4612204377badadd62cb0e5c3d
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618138B2

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