2-Bromobut-2-ene → 3-Phenyl-5-(1-hydroxy-2-methyl-2-butenyl)isoxazole

HRID 1440337ノート

反応式

HRID 1440337 の反応式
[C:1]1([C:7]2[CH:11]=[C:10]([CH:12]=[O:13])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Mg].Br[C:16](=[CH:18][CH3:19])[CH3:17].[Cl-].[NH4+]>O1CCCC1.O>[C:1]1([C:7]2[CH:11]=[C:10]([CH:12]([OH:13])[C:16]([CH3:17])=[CH:18][CH3:19])[O:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

7

反応物 4

HCID 209102-Bromobut-2-eneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 113672673-Phenyl-1,2-oxazole-5-carbaldehyde

生成物 1

HCID 536910293-Phenyl-5-(1-hydroxy-2-methyl-2-butenyl)isoxazole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 5.0 g (28.9 mmol) of 3-phenyl-isoxazole-5-aldehyde in 40 ml of tetrahydrofuran, was added dropwise at -30° C. a solution of 1.5 g of metallic magnesium and 10.1 g (74.8 mmol) of 2-bromo-2-butene in 80 ml of tetrahydrofuran. After they were reacted at the same temperature for 30 minutes, the temperature of the reaction mixture was allowed to rise to room temperature and a saturated aqueous solution of ammonium chloride was added to terminate the reaction. Water was added, followed by extraction with ethyl ether. The organic layer was successively washed with water and saturated saline and then dried over anhydrous sodium sulfate. After ethyl ether was distilled off, the residue was purified by chromatography on a silica gel column (eluent: 9:1 hexane/ethyl acetate) so that 3-phenyl-5-(1-hydroxy-2-methyl-2-butenyl)isoxazole was obtained as oil.

後処理

  1. customAfter they were reacted at the same temperature for 30 minutes
  2. customto rise to room temperature
  3. customto terminate
  4. customthe reaction
  5. extractionfollowed by extraction with ethyl ether
  6. washThe organic layer was successively washed with water and saturated saline
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter ethyl ether was distilled off
  9. customthe residue was purified by chromatography on a silica gel column (eluent: 9:1 hexane/ethyl acetate) so that 3-phenyl-5-(1-hydroxy-2-methyl-2-butenyl)isoxazole
  10. customwas obtained as oil

出典と根拠

ORDレコード
ord-bdf087cc2f9a4c1682eec862b99bdf8c
出典データセット
uspto-grants-1996_03
特許番号
US05498619

反応ノート

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