Triethylamine → 3-(4-Nitro-phenyl)-isoxazole-5-carboxylic acid ethyl ester

HRID 75759

반응식

HRID 75759 반응식
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[C:15]#[CH:16].CCN(CC)CC>C1(C)C=CC=CC=1.CCOC(C)=O>[CH2:19]([O:18][C:14]([C:15]1[O:1][N:2]=[C:3]([C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=2)[CH:16]=1)=[O:17])[CH3:20]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 12182Ethyl propiolateHCID 915274alpha-Chloro-4-nitrobenzaldoxime

생성물 1

HCID 9493753-(4-Nitro-phenyl)-isoxazole-5-carboxylic acid ethyl ester수율 51.7%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To a solution of N-hydroxy-4-nitro-benzimidoyl chloride (2.0 g; 10 mmol) and ethyl propiolate (2.02 ml; 20 mmol) in toluene (25 ml) was added Et3N (1.46 ml; 10.5 mmol) drop wise for 10 minutes. The resulting reaction mixture was heated at 80° C. for 2.5 hours, and then diluted with EtOAc (50 ml) and transferred in a separating funnel. The EtOAc layer was washed with 0.1N HCl (10 ml) followed by water (3×10 ml) and brine (10 ml). The EtOAc layer was dried over anhydrous Na2SO4, solvent was evaporated and the residue was crystallized from CHCl3 and light petroleum to afford the title compound of step 1 (1.35 g; 51.7%). Mass (ES+), 263 (M++1); 1H NMR (CDCl3) δ: 1.45 (t, 3H), 4.48 (q, 2H), 7.26 (s, 1H), 8.02 (d, 2H), 8.35 (d, 2H).

후처리

  1. customThe resulting reaction mixture
  2. customtransferred in a separating funnel
  3. washThe EtOAc layer was washed with 0.1N HCl (10 ml)
  4. dry with materialThe EtOAc layer was dried over anhydrous Na2SO4, solvent
  5. customwas evaporated
  6. customthe residue was crystallized from CHCl3 and light petroleum

출처 및 근거

ORD 기록
ord-4057b49b7fde4dd7b211e637d8014c1a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835428B2

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