Dabco → Ethyl 5-cyclopropylisoxazole-3-carboxylate

HRID 58531

반응식

HRID 58531 반응식
[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

참가 물질

5

반응물 3

HCID 9237DabcoHCID 69379Ethyl nitroacetateHCID 138823Cyclopropylacetylene

생성물 1

HCID 55251041Ethyl 5-cyclopropylisoxazole-3-carboxylate수율 92.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9e524bd03fb64855931146cbd86ab99c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434722B2

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