Potassium Carbonate → 5-Methyl-3-(4-aminophenoxymethyl)isoxazole

HRID 1725663노트

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HRID 1725663 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl>[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 605945865-Methyl-3-(4-nitrophenoxymethyl)isoxazole

생성물 1

HCID 610283115-Methyl-3-(4-aminophenoxymethyl)isoxazole수율 46%

시약·촉매·용매 1

HCID 21226129Dichloromethane methanol용매

실험 절차

The 5-methyl-3-(4-nitrophenoxymethyl)isoxazole (3, X═H) (2.59 g, 11.07 mmol) was dissolved in MeOH:CH2Cl2 (1:1, 600 mL). An aqueous solution of (77 mL) sodium hydrosulfite (11.93 g, 68.5 mmol) and K2CO3 (9.55 g, 69 mmol) was added dropwise under nitrogen for 30 min. The reaction was allowed to stir at room temperature for 2 h, and the organic solvents were removed under reduced pressure, diluted with water (200 mL), extracted with CH2Cl2 (3×300 mL), dried over anhydrous Na2SO4 and solvent was removed under reduced pressure. The resulting product was finally dried under high vacuum to afford 1.03 g (46%) of the 5-methyl-3-(4-aminophenoxymethyl)isoxazole (4, X═H). 1H NMR (CDCl3): δ 6.78 (d, 2H, J=8.7 Hz), 6.61 (d, 2H, J=8.4 Hz), 6.07 (s, 1H), 5.01 (s, 2H), 3.44 (s, 2H), 2.40 (s, 3H); LCMS (m/z): 205 (MH+).

후처리

  1. customthe organic solvents were removed under reduced pressure
  2. additiondiluted with water (200 mL)
  3. extractionextracted with CH2Cl2 (3×300 mL)
  4. dry with materialdried over anhydrous Na2SO4 and solvent
  5. customwas removed under reduced pressure
  6. customThe resulting product was finally dried under high vacuum

출처 및 근거

ORD 기록
ord-0632ef84163f4a67b458289f08ac8701
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491732B2

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