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

HRID 524415ノート

反応式

HRID 524415 の反応式
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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 25134Boron tribromide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f8727927b39949abb06e4d09e49ae0ab
出典データセット
uspto-grants-2016_05
特許番号
US09340506B2

反応ノート

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