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

HRID 1031781노트

반응식

HRID 1031781 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

(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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0fc8471770dc4d5ba87f076533fe9750
출처 데이터셋
uspto-grants-1990_09
특허 번호
US04954647

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