Dabco → Ethyl 5-cyclopropylisoxazole-3-carboxylate

HRID 58531

反応式

HRID 58531 の反応式
[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

参加物

5

反応物 3

HCID 9237DabcoHCID 69379Ethyl nitroacetateHCID 138823Cyclopropylacetylene

生成物 1

HCID 55251041Ethyl 5-cyclopropylisoxazole-3-carboxylate収率 92.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9e524bd03fb64855931146cbd86ab99c
出典データセット
uspto-grants-2016_09
特許番号
US09434722B2

関連ノート

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