Hydrochloric Acid → 5-(4-Trifluoromethylphenyl)-4-isoxazolylmethanol

HRID 1794326ノート

反応式

HRID 1794326 の反応式
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[C:14](OCC)=[O:15])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][OH:15])=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22221374Ethyl 5-(4-trifluoromethylphenyl)isoxazole-4-carboxylate

生成物 1

HCID 222214255-(4-Trifluoromethylphenyl)-4-isoxazolylmethanol収率 97%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl 5-(4-trifluoromethylphenyl)isoxazole-4-carboxylate (7.63 g) in tetrahydrofuran (100 ml) was gently added diisobutylaluminum hydride (1.0 M hexane solution, 59 ml) at 0° C. and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give 5-(4-trifluoromethylphenyl)-4-isoxazolylmethanol (6.29 g, yield 97%) as colorless crystals. The crystals were recrystallized from ethyl acetate-hexane to give a colorless prism. melting point: 106–107° C.

後処理

  1. customat 0° C.
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-cdcc21efe7934eb49cfb056072976335
出典データセット
uspto-grants-2006_04
特許番号
US07022725B2

反応ノート

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