4-Toluenesulfonyl chloride → (R)-4-(Methylthio)-2-(p-toluenesulfonyloxy)butyl p-Toluenesulfonate

HRID 2352047ノート

反応式

HRID 2352047 の反応式
[CH3:1][S:2][CH2:3][CH2:4][C@@H:5]([OH:8])[CH2:6][OH:7].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([O:7][CH2:6][C@H:5]([O:8][S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH2:4][CH2:3][S:2][CH3:1])(=[O:17])=[O:16])=[CH:11][CH:10]=1

参加物

4

反応物 2

HCID 73974-Toluenesulfonyl chlorideHCID 10920564(R)-4-(methylthio)1,2-butanediol

生成物 1

HCID 14634101(R)-4-(Methylthio)-2-(p-toluenesulfonyloxy)butyl p-Toluenesulfonate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

(R)-4-(Methylthio)-1,2-butanediol (0.4 g, 2.9 mmol) was dissolved in 5 ml of pyridine and cooled to 0°-5° C. p-Toluenesulfonyl chloride (1.65 g, 9.0 mmol) was added and, after 5 minutes, the cooling bath removed, and the mixture stirred at room temperature for 2 hours, at which point it was diluted with 15 ml of H2O and extracted with 20 ml of ethyl acetate. The organic extract was washed with saturated NaCl, dried (MgSO4) and stripped to yield 0.5 g of present, crude title product as an oil, all of which was used in the next step without further refinement; tlc Rf 0.53 (3:1 hexane:ethyl acetate), 0.25 (5:1 hexane:ethyl acetate).

後処理

  1. additionwas added and, after 5 minutes
  2. customthe cooling bath removed
  3. additionwas diluted with 15 ml of H2O
  4. extractionextracted with 20 ml of ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with saturated NaCl
  7. dry with materialdried (MgSO4)

出典と根拠

ORDレコード
ord-9fd57818a98044eeaeae07c3e1962870
出典データセット
uspto-grants-1989_10
特許番号
US04874877

反応ノート

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