4-Toluenesulfonyl chloride → HCID 18411913、化合物

HRID 896526ノート

反応式

HRID 896526 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>N1C=CC=CC=1>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][O:11][S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:24])=[CH:15][CH:16]=2)(=[O:22])=[O:21])=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 112755102-(4-(Trifluoromethyl)phenyl)ethan-1-ol

生成物 1

HCID 18411913HCID 18411913、化合物収率 80%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of 2-(4-trifluoromethylphenyl)-ethanol (570 mg, 3.0 mmol) in pyridine (6 mL) was stirred on an ice/acetone bath and treated with p-toluenesulfonyl chloride (630 mg, 3.3 mmol). The cooling bath was replaced with an ice/water bath and the mixture was stirred for 3.5 hours. Ice-cold water (12 mL) was added slowly, and the mixture was extracted three times with chloroform. The combined organic phases were washed with water, then with cold 1.0 N aqueous sulfuric acid until the wash phase was acidic. The organic phase was dried over sodium sulfate and concentrated to provide a white solid (826 mg) which contained about 10% by weight of residual alcohol. This was used without further purification. 1H NMR (300 MHz, CDCl3) for toluenesulfonate: δ7.65 (d, J=8 Hz, 2H), 7.50 (d, J=8 Hz, 2H), 7.26 (d, J=8 Hz, 2H), 7.23 (d, J=8 Hz, 2H), 4.26 (t, J=7 Hz, 2H), 3.02 (t, J=7 Hz, 2H), 2.44 (s, 3H).

後処理

  1. customThe cooling bath was replaced with an ice/water bath
  2. extractionthe mixture was extracted three times with chloroform
  3. washThe combined organic phases were washed with water
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-ade26f5432b84c6bb841dbadd5e0ba2d
出典データセット
uspto-grants-2005_07
特許番号
US06919356B2

反応ノート

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