Tetrahydrofuran → 4-Chloromethyl-5-(4-trifluoromethylphenyl)isoxazole

HRID 1794327ノート

反応式

HRID 1794327 の反応式
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14]O)=[CH:5][CH:4]=1.O1CCCC1.S(Cl)([Cl:25])=O>C1(C)C=CC=CC=1>[Cl:25][CH2:14][C:10]1[CH:11]=[N:12][O:13][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 222214255-(4-Trifluoromethylphenyl)-4-isoxazolylmethanol

生成物 1

HCID 222211934-Chloromethyl-5-(4-trifluoromethylphenyl)isoxazole収率 77.3%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a mixture of 5-(4-trifluoromethylphenyl)-4-isoxazolylmethanol (5.65 g), tetrahydrofuran (20 ml) and toluene (80 ml) was added dropwise thionyl chloride (4.15 g) at 0° C. and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, saturated aqueous sodium hydrogencarbonate was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained colorless crystals were filtrated and recrystallized from ethyl acetate-hexane to give 4-chloromethyl-5-(4-trifluoromethylphenyl)isoxazole (4.70 g, yield 77%) as a colorless prism. melting point: 99–100° C.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additionsaturated aqueous sodium hydrogencarbonate was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. filtrationThe obtained colorless crystals were filtrated
  8. customrecrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-dbc12715e25745b9986b950177d78cbb
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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