Potassium Hydroxide → 2-(4-Amino-3-ethyl-5-methylphenyl)-1,1,1,3,3,4,4,4-octafluorobutan-2-ol

HRID 1970847ノート

反応式

HRID 1970847 の反応式
[CH2:1]([C:3]1[CH:8]=[C:7]([C:9](F)([C:17]([F:20])([F:19])[F:18])[C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH:6]=[C:5]([CH3:22])[C:4]=1[NH2:23])[CH3:2].[OH-:24].[K+]>C(#N)C.O>[NH2:23][C:4]1[C:5]([CH3:22])=[CH:6][C:7]([C:9]([OH:24])([C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[C:17]([F:20])([F:19])[F:18])=[CH:8][C:3]=1[CH2:1][CH3:2]

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 866652892-Ethyl-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-6-methylaniline

生成物 1

HCID 866652882-(4-Amino-3-ethyl-5-methylphenyl)-1,1,1,3,3,4,4,4-octafluorobutan-2-ol収率 60%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

To a solution of 2-ethyl-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-6-methyl-phenylamine (prepared as descriebed in WO 2008/074427) (3.88 g, 11 mmol) in a mixture of acetonitrile (320 ml) and water (80 ml) was added potassium hydroxide (46.2 g, 827 mmol). The reaction mixture was stirred at 70° C. for 2 days. The reaction mixture was diluted with water (200 ml) and the mixture extracted three times with ethyl acetate (200 ml). The combined organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:3) to give 2-(4-amino-3-ethyl-5-methylphenyl)-1,1,1,3,3,4,4,4-octafluorobutan-2-ol (2.31 g, 60% yield). LC-MS (Method 1): RT=1.87, [M−H]−=352.

後処理

  1. extractionthe mixture extracted three times with ethyl acetate (200 ml)
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:3)

出典と根拠

ORDレコード
ord-c6c7339c8653491baace3b4dec548af6
出典データセット
uspto-grants-2013_04
特許番号
US08431514B2

反応ノート

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