4-Isopropoxy-3-(trifluoromethyl)benzoic acid → (4-(5-(4-Isopropoxy-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-3-yl)phenyl)methanol

HRID 454798ノート

反応式

HRID 454798 の反応式
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])([CH3:3])[CH3:2].O[N:19]=[C:20]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=1)[NH2:21]>C1COCC1>[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]2[O:11][N:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][OH:29])=[CH:24][CH:23]=3)[N:19]=2)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 225977674-Isopropoxy-3-(trifluoromethyl)benzoic acidHCID 53437716N-Hydroxy-4-(hydroxymethyl)benzimidamide

生成物 1

HCID 69669389(4-(5-(4-Isopropoxy-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-3-yl)phenyl)methanol収率 55.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-isopropoxy-3-(trifluoromethyl)benzoic acid (CAS 213598-16-4)(1.04 g, 4.19 mmol) in THF (20 mL) was added CU (748 mg, 4.61 mmol). After stirring at rt for 2 h, N′-hydroxy-4-(hydroxymethyl)benzenecarboximidamide (CAS 1233243-49-6) (766 mg, 4.61 mmol) was added to the mixture and resulting solution was stirred at 50° C. for 3 h. The reaction mixture was submitted to the microwave at 150° C. for 20 min. The reaction mixture was quenched with water, extracted with EtOAc and washed with K2CO3, brine, dried over magnesium sulfate and concentrated. The crude material was purified by MPLC (1:1 ethyl acetate in hexanes) to give rise to 874 mg of the title compound as a colorless solid.

後処理

  1. customresulting solution
  2. stirringwas stirred at 50° C. for 3 h
  3. waitThe reaction mixture was submitted to the microwave at 150° C. for 20 min
  4. customThe reaction mixture was quenched with water
  5. extractionextracted with EtOAc
  6. washwashed with K2CO3, brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe crude material was purified by MPLC (1:1 ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-8bcc436e80ee420485fc3fb68937ebf7
出典データセット
uspto-grants-2013_07
特許番号
US08497255B2

反応ノート

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