Ethyl 3-(4-methoxyphenyl)isoxazole-5-carboxylate → Ethyl 3-(4-hydroxyphenyl)isoxazole-5-carboxylate

HRID 524415노트

반응식

HRID 524415 반응식
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:11][N:10]=2)=[CH:5][CH:4]=1>C(Cl)Cl.B(Br)(Br)Br>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:13]=[C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:11][N:10]=2)=[CH:7][CH:8]=1

참가 물질

4

반응물 1

HCID 776513Ethyl 3-(4-methoxyphenyl)isoxazole-5-carboxylate

생성물 1

HCID 136133842Ethyl 3-(4-hydroxyphenyl)isoxazole-5-carboxylate수율 74.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 25134Boron tribromide용매

실험 절차

To a stirred solution of ethyl 3-(4-methoxyphenyl)isoxazole-5-carboxylate (1 g, 4.04 mmol, prepared according to literature method Tet. Lett 2009, 50(27), 3948-3951) in 8 mL DCM, Boron tribromide 1 M solution in DCM (8.0 mL, 8.08 mmol) was added dropwise at −78° C. After complete addition reaction mixture was allowed to warm slowly and further stirred for 16 hrs at RT. After completion of the reaction, solvent was removed under reduced pressure. The reaction mixture was diluted with ice cold water (20 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with water, brine and dried over sodium sulfate, filtered and concentrated under reduced pressure to get ethyl 3-(4-hydroxyphenyl)isoxazole-5-carboxylate (0.7 g).

후처리

  1. additionAfter complete addition reaction mixture
  2. temperatureto warm slowly
  3. customAfter completion of the reaction, solvent
  4. customwas removed under reduced pressure
  5. additionThe reaction mixture was diluted with ice cold water (20 mL)
  6. extractionextracted with ethyl acetate (3×50 mL)
  7. washThe combined organic layer was washed with water, brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-f8727927b39949abb06e4d09e49ae0ab
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340506B2

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