3-Methyl-but-2-enoic acid 4-bromo-phenyl ester → 2H-1-Benzopyran-2-one, 6-bromo-3,4-dihydro-4,4-dimethyl-

HRID 51662

반응식

HRID 51662 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9](=[O:14])[CH:10]=[C:11]([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[O:8][C:9](=[O:14])[CH2:10][C:11]2([CH3:12])[CH3:13]

참가 물질

4

반응물 2

HCID 7337973-Methyl-but-2-enoic acid 4-bromo-phenyl esterHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 225689232H-1-Benzopyran-2-one, 6-bromo-3,4-dihydro-4,4-dimethyl-수율 59.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 3-methyl-but-2-enoic acid 4-bromo-phenyl ester (7 g, 27.6 mmol) in anhydrous dichloromethane (200 mL) was cooled (ice bath) and treated with aluminum chloride (6.6 g, 49.6 mmol) and the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was quenched with saturated aqueous sodium bicarbonate solution and extracted with diethyl ether (×2). The combined organic extract was washed woth brine (×1), dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford an oil which was purified by flash column chromatography over silica gel (230-400 mesh) using 2.5% ethyl acetate in hexane as the eluent to afford the title compound (4.2 g, 57%).

후처리

  1. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate solution
  2. extractionextracted with diethyl ether (×2)
  3. extractionThe combined organic extract
  4. washwas washed woth brine (×1)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto afford an oil which
  9. customwas purified by flash column chromatography over silica gel (230-400 mesh)

출처 및 근거

ORD 기록
ord-185915a746414c478613f937a8c5f1b5
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713647B2

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