Citric Acid → 4-(2-Bromo-5-fluorophenyl)-2-hydroxy-4-methylvaleric acid-methyl ester

HRID 1374621ノート

反応式

HRID 1374621 の反応式
[CH3:1][O:2][C:3](=[O:25])[CH:4](C(=O)C1C=CC=CC=1)[CH2:5][C:6]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[Br:16])([CH3:8])[CH3:7].C(=O)([O-])[O-:27].[K+].[K+].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].CI.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.CC(OC)(C)C>[CH3:1][O:2][C:3](=[O:25])[CH:4]([OH:27])[CH2:5][C:6]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[Br:16])([CH3:8])[CH3:7]

参加物

9

反応物 6

HCID 311Citric AcidHCID 1118Sulfuric AcidHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 695164952-Benzoyl-4-(2-bromo-5-fluorophenyl)-4-methylvaleric acid-methyl ester

生成物 1

HCID 695167344-(2-Bromo-5-fluorophenyl)-2-hydroxy-4-methylvaleric acid-methyl ester収率 36.8%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 15413tert-Butyl methyl ether溶媒

実験手順

A solution of 0.9 g (2.13 mmol) of 2-benzoyl-4-(2-bromo-5-fluorophenyl)-4-methylvaleric acid-methyl ester in 50 ml of MeOH is mixed with 1.47 g (10.6 mmol) of potassium carbonate and stirred for 3 hours at room temperature. The batch is acidified (pH 3) with 10% sulfuric acid, and it is extracted with ethyl acetate. The combined extracts are washed with saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is taken up in 8 ml of DMF and stirred with 1.92 g (5.9 mmol) of cesium carbonate and 0.38 ml. (5.9 mmol) of methyl iodide for 3 hours at room temperature. The batch is mixed with 10% citric acid and extracted-with MTBE. The organic phase is washed with saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 250 mg of product.

後処理

  1. extractionis extracted with ethyl acetate
  2. washThe combined extracts are washed with saturated NaCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum
  5. washThe organic phase is washed with saturated NaCl
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by evaporation in a vacuum

出典と根拠

ORDレコード
ord-831341dffb94456785663c930bfed1f1
出典データセット
uspto-grants-2007_01
特許番号
US07166592B2

反応ノート

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