Ethyl Acetate → 6-Bromo-8-hydroxy-2,2,4,4-tetramethyl chroman

HRID 2377332ノート

反応式

HRID 2377332 の反応式
C([O:4][C:5]1[CH:6]=[C:7]([Br:19])[CH:8]=[C:9]2[C:14]=1[O:13][C:12]([CH3:16])([CH3:15])[CH2:11][C:10]2([CH3:18])[CH3:17])(=O)C.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>CO.CCCCCC>[Br:19][C:7]1[CH:8]=[C:9]2[C:14](=[C:5]([OH:4])[CH:6]=1)[O:13][C:12]([CH3:16])([CH3:15])[CH2:11][C:10]2([CH3:18])[CH3:17]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 574242158-Acetoxy-6-bromo-2,2,4,4-tetramethyl chroman2 回

生成物 1

HCID 574242146-Bromo-8-hydroxy-2,2,4,4-tetramethyl chroman収率 84%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8058Hexane溶媒

実験手順

A solution of 8-acetoxy-6-bromo-2,2,4,4-tetramethyl chroman (Intermediate 16, 1.3 g, 3.98 mmol) in methanol was treated with sodium carbonate (0.8 g, 7.95 mmol) and the resulting reaction mixture was stirred at ambient temperature overnight. The volatiles were evaporated in vacuo, the residue was diluted with water and extracted with ethyl acetate. The organic phase was dried over anhydrous magnesium 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 product as an oil (0.95 g, 84%).

後処理

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue was diluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. 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-608c77b5df284771a63942b6fa35b89e
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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