Dichloromethane → 8-Acetoxy-6-bromo-2,2,4,4-tetramethyl chroman

HRID 2377331ノート

反応式

HRID 2377331 の反応式
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.ClCCl.ClC1C=[C:25](C=CC=1)[C:26]([O:28]O)=[O:27].C(OCC)(=O)C>CCCCCC>[C:26]([O:28][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:27])[CH3:25]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 70297m-Chloroperbenzoic acidHCID 211072398-Acetyl-6-bromo-2,2,4,4-tetramethyl chroman2 回

生成物 1

HCID 574242158-Acetoxy-6-bromo-2,2,4,4-tetramethyl chroman収率 92%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

実験手順

A solution of 8-acetyl-6-bromo-2,2,4,4-tetramethyl chroman (Intermediate 15A, 1.3 g, 4.18 mol) in anhydrous dichloromethane (30 mol) 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%).

後処理

  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)

出典と根拠

ORDレコード
ord-9f21925dd17e44a9acc40f1194f99d1a
出典データセット
uspto-grants-2008_12
特許番号
US07468391B2

反応ノート

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