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

HRID 1770814ノート

反応式

HRID 1770814 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 610283115-Methyl-3-(4-aminophenoxymethyl)isoxazole収率 46%

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-e3cf0e5f4ae24e7eacb08fb2a56d3d25
出典データセット
uspto-grants-2016_02
特許番号
US09248190B2

反応ノート

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