Sodium Hydroxide → 4-(Morpholin-3-on-4-yl)-3-trifluoromethyl-benzoic acid

HRID 1629813ノート

反応式

HRID 1629813 の反応式
[N:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=2[C:16]([F:19])([F:18])[F:17])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[OH-].[Na+].[Mn]([O-])(=O)(=O)=[O:23].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>O>[N:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=2[C:16]([F:17])([F:19])[F:18])[CH2:6][CH2:5][O:4][CH2:3][C:2]1=[O:23]

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 516875Potassium PermanganateHCID 594957964-Morpholin-4-yl-3-(trifluoromethyl)benzoic acid

生成物 1

HCID 670485144-(Morpholin-3-on-4-yl)-3-trifluoromethyl-benzoic acid

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
45 °C

実験手順

1.00 g (3.63 mmol) 4-(morpholin-4-yl)-3-trifluoromethyl-benzoic acid (prepared by synthesis sequence analogously to Example 13a and 13b) is suspended in 40 ml of water and 150 mg (3.75 mmol) sodium hydroxide are added. Then 1.73 g (10.92 mmol) potassium permanganate are added and the mixture is stirred for 1.5 hours at 45° C. Then the reaction mixture is cooled in the ice bath and sodium thiosulphate is added until total decolorisation is obtained. After extraction 3 times with ethyl acetate the combined organic phases are dried over sodium sulphate evaporated down i. vac. After application of the residue to silica gel it is purified by chromatography on silica gel (eluant: dichloromethane/methanol 95:5).

後処理

  1. additionis added until total decolorisation
  2. customis obtained
  3. extractionAfter extraction 3 times with ethyl acetate the combined organic phases
  4. dry with materialare dried over sodium sulphate
  5. customevaporated down i
  6. customAfter application of the residue to silica gel it is purified by chromatography on silica gel (eluant: dichloromethane/methanol 95:5)

出典と根拠

ORDレコード
ord-096037be32bc4a888d407fe06a43f3ed
出典データセット
uspto-grants-2014_07
特許番号
US08791103B2

反応ノート

読み込み中…