Ethyl Acetate → 8-Acetoxy-6-bromo-2,2,4,4-tetramethyl chroman

HRID 1869851노트

반응식

HRID 1869851 반응식
C([C:4]1[CH:5]=[C:6]([Br:18])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH3:15])([CH3:14])[CH2:10][C:9]2([CH3:17])[CH3:16])(=O)C.ClC1C=[C:22](C=CC=1)[C:23]([O:25]O)=[O:24].C(OCC)(=O)C>ClCCl.CCCCCC>[C:23]([O:25][C:4]1[CH:5]=[C:6]([Br:18])[CH:7]=[C:8]2[C:13]=1[O:12][C:11]([CH3:14])([CH3:15])[CH2:10][C:9]2([CH3:16])[CH3:17])(=[O:24])[CH3:22]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 211072398-Acetyl-6-bromo-2,2,4,4-tetramethyl chroman2회

생성물 1

HCID 574242158-Acetoxy-6-bromo-2,2,4,4-tetramethyl chroman수율 95%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

A solution of 8-acetyl-6-bromo-2,2,4,4-tetramethyl chroman (Intermediate 15A, 10.3 g, 4.18 mmol) in anhydrous dichloromethane (30 mL) was treated with a 77% aqueous solution of 3-chloroperoxybenzoic acid (5.75 g, 33.44 mmol) and the resulting reaction mixture was stirred at ambient temperature for 24 h. The reaction mixture was then cooled in an ice bath and cautiously quenched with saturated sodium thiosulfate solution. The phases were separated and the organic phase was washed with saturated, aqueous sodium bicarbonate solution, water and brine, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford a residue that on flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent afforded the title compound as an oil (1.3 g, 92%).

후처리

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was then cooled in an ice bath
  3. customcautiously quenched with saturated sodium thiosulfate solution
  4. customThe phases were separated
  5. washthe organic phase was washed with saturated, aqueous sodium bicarbonate solution, water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto afford a residue that on flash column chromatography over silica gel (230-400 mesh)

출처 및 근거

ORD 기록
ord-70e03cd572a44c889004dc3f55095bc0
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638648B2

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