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

HRID 1794327노트

반응식

HRID 1794327 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 222211934-Chloromethyl-5-(4-trifluoromethylphenyl)isoxazole수율 77.3%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dbc12715e25745b9986b950177d78cbb
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022725B2

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