3-Hydroxybutyrolactone, (3S)- → (3S)-3-acetyloxy-4-bromobutanoic acid

HRID 1595029

反応式

HRID 1595029 の反応式
[OH:1][C@@H:2]1[CH2:7][O:6][C:4](=[O:5])[CH2:3]1.[BrH:8].[C:9]([OH:12])(=O)[CH3:10]>C(Cl)Cl>[C:9]([O:1][C@H:2]([CH2:7][Br:8])[CH2:3][C:4]([OH:6])=[O:5])(=[O:12])[CH3:10]

参加物

4

反応物 2

HCID 72693893-Hydroxybutyrolactone, (3S)-HCID 21893785Acetic Acid Mixture with Hydrobromic Acid

生成物 1

HCID 2733880(3S)-3-acetyloxy-4-bromobutanoic acid収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (S)-3-hydroxybutyrolactone (10 g) in 85% purity and hydrogen bromide/acetic acid (40 ml) in 30% purity was charged to a 250 ml flask equipped with a thermometer, reflux condensor and agitator, and stirred at 40˜60° C. for 5 hours. After the reaction was completed, the reaction solution was cooled at room temperature. With the addition of methylene chloride (200 ml), the mixture washed with 1M sodium acetate solution and then an organic layer was separated, dried over anhydrous magnesium sulfate, filtered off and concentrated. Toluene (100 ml) was added to (S)-3-acetoxy-4-bromobutyric acid, so concentrated, to remove the remaining acetic acid. The concentration under reduced pressure gave 18.74 g of (S)-3-acetoxy-4-bromobutyric acid (yield: 85%).

後処理

  1. customequipped with a thermometer
  2. temperaturereflux condensor and agitator
  3. washthe mixture washed with 1M sodium acetate solution
  4. customan organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered off
  7. concentrationconcentrated
  8. additionToluene (100 ml) was added to (S)-3-acetoxy-4-bromobutyric acid
  9. concentrationso concentrated
  10. customto remove the remaining acetic acid
  11. concentrationThe concentration under reduced pressure

出典と根拠

ORDレコード
ord-94ed71b06d154bec8e4a27635cdd4997
出典データセット
uspto-grants-2001_09
特許番号
US06284902B1

関連ノート

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