4-Toluenesulfonyl chloride → (3-Chloroprop-1-yn-1-yl)benzene

HRID 617836

反応式

HRID 617836 の反応式
[C:1]1([C:7]#[C:8][CH2:9]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S([Cl:21])(C1C=CC(C)=CC=1)(=O)=O>N1C=CC=CC=1>[C:1]1([C:7]#[C:8][CH2:9][Cl:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 1231153-Phenyl-2-propyn-1-ol

生成物 1

HCID 287343(3-Chloroprop-1-yn-1-yl)benzene収率 63%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

1-Phenyl-1-propyn-3-ol (5 g), 5.1 g of tosyl chloride and 20 ml of pyridine were stirred at room temperature for 1 hour. The reaction mixture was poured into 100 ml of ice water and extracted with ethyl acetate. The oil layer was washed with 1 N hydrochloric acid and saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled away. The residue was purified by silica gel column chromatography (ethyl acetate:hexane 1:5) to give 2.54 g of 3-phenyl-2-propynyl chloride as a pale yellow, oily substance.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe oil layer was washed with 1 N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled away
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane 1:5)

出典と根拠

ORDレコード
ord-73c4a82ac4f2473c9c3df8f241921ac9
出典データセット
uspto-grants-1999_09
特許番号
US05952316

関連ノート

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