Sodium Hydroxide → (3R)-2-(4-ethylphenyl)-4,4,4-trifluoro-3-methylbutanoic acid

HRID 2402362ノート

反応式

HRID 2402362 の反応式
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C@@H:15]([CH3:20])[C:16]([F:19])([F:18])[F:17])[C:10]([O:12]CC)=[O:11])=[CH:5][CH:4]=1)[CH3:2].[OH-].[Na+]>CO.C1COCC1.O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]([C@@H:15]([CH3:20])[C:16]([F:17])([F:18])[F:19])[C:10]([OH:12])=[O:11])=[CH:7][CH:8]=1)[CH3:2]

参加物

6

反応物 2

HCID 14798Sodium HydroxideHCID 58288230Ethyl(3R)-2-(4-ethylphenyl)-4,4,4-trifluoro-3-methylbutanoate

生成物 1

HCID 58288296(3R)-2-(4-ethylphenyl)-4,4,4-trifluoro-3-methylbutanoic acid

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

3.0 g of ethyl (3R)-2-(4-ethylphenyl)-4,4,4-trifluoro-3-methylbutanoate (purity about 88%, about 9.16 mmol; diastereomer mixture) were dissolved in the mixture of in each case 12.4 ml of methanol, THF and water, and 5.49 g (137.35 mmol) of sodium hydroxide were added a little at a time. The reaction mixture was stirred at 40° C. for 9 h. After cooling, the volatile solvents were substantially removed under reduced pressure and the residue was diluted with water. The mixture was acidified by addition of hydrochloric acid, and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate, and concentrated under reduced pressure, and the residue was dried under high vacuum. This gave 2.61 g of the title compound as a crude product which was not purified any further (diastereomer ratio about 9:1).

後処理

  1. additionwere added a little at a time
  2. temperatureAfter cooling
  3. customthe volatile solvents were substantially removed under reduced pressure
  4. additionthe residue was diluted with water
  5. additionThe mixture was acidified by addition of hydrochloric acid
  6. extractionthe aqueous phase was extracted three times with ethyl acetate
  7. dry with materialThe combined organic phases were dried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was dried under high vacuum
  10. customThis gave 2.61 g of the title compound as a crude product which was not purified any further (diastereomer ratio about 9:1)

出典と根拠

ORDレコード
ord-c02992d21bef42cc9eebde9952dcfc77
出典データセット
uspto-grants-2014_08
特許番号
US08796335B2

反応ノート

読み込み中…