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

HRID 1450658노트

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HRID 1450658 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 5.0 g (28.9 mmol) of 3-phenylisoxazole-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.

후처리

  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

출처 및 근거

ORD 기록
ord-916a2f8826c34233a0d386a3cfce4276
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05602160

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