Water → 4,6-Di-tert-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran

HRID 1452361노트

반응식

HRID 1452361 반응식
C([O:4][C:5]1[C:10]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:9][C:8]([OH:15])=[C:7]([CH2:16][CH:17]=[CH2:18])[C:6]=1[C:19]([CH3:22])([CH3:21])[CH3:20])(=O)C.B(F)(F)F.O.[OH-].[Na+]>ClCCl>[C:19]([C:6]1[C:7]2[CH2:16][CH:17]([CH3:18])[O:15][C:8]=2[CH:9]=[C:10]([C:11]([CH3:14])([CH3:12])[CH3:13])[C:5]=1[OH:4])([CH3:20])([CH3:21])[CH3:22]

참가 물질

6

반응물 4

HCID 962Water2회HCID 6356Boron trifluorideHCID 14798Sodium HydroxideHCID 111202654-Acetoxy-3,5-di-tert-butyl-2-(2-propenyl)phenol

생성물 1

HCID 184331834,6-Di-tert-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran수율 52%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-Acetoxy-3,5-di-tert-butyl-2-(2-propenyl)phenol (1.0 g, 3.3 mmol) was dissolved in dichloromethane (10 ml) and BF3 etherate (0.7 ml) was added dropwise to the solution under a nitrogen atmosphere. The mixture was stirred for 24 h at room temperature and, thereafter, water was added and the mixture was extracted with ethyl acetate. The extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate, dried over anhydrous magnesium sulfate and concentrated. The concentrate was dissolved in tetrahydrofuran (5 ml) and the solution was added dropwise to a suspension of lithium aluminum hydride (76 mg) in tetrahydrofuran (5 ml) that had been prepared under a nitrogen atmosphere. After refluxing for 3 h, the reaction mixture was cooled to room temperature and water was added dropwise. Following the addition of 1N aqueous sodium hydroxide, the mixture was subjected to extraction with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4,6-di-tert-butyl-5-hydroxy-2-methyl-2,3-dihydrobenzofuran [450 mg (yield, 52%)].

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extracted layer was washed with a saturated aqueous solution of sodium hydrogen carbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe concentrate was dissolved in tetrahydrofuran (5 ml)
  6. additionthe solution was added dropwise to a suspension of lithium aluminum hydride (76 mg) in tetrahydrofuran (5 ml) that
  7. customhad been prepared under a nitrogen atmosphere
  8. temperatureAfter refluxing for 3 h
  9. temperaturethe reaction mixture was cooled to room temperature
  10. extractionthe mixture was subjected to extraction with diethyl ether
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. concentrationconcentrated
  13. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)

출처 및 근거

ORD 기록
ord-1b5ae96c58814f61a30120ff55032ec0
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05606089

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