4-Toluenesulfonyl chloride → (2S)-(4E)-5-(3-pyridyl)-4-penten-2-ol p-toluenesulfonate

HRID 1824741

반응식

HRID 1824741 반응식
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](/[CH:18]=[CH:19]/[CH2:20][C@@H:21]([OH:23])[CH3:22])[CH:13]=1.C([O-])(O)=O.[Na+]>C(N(CC)CC)C>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:23][C@H:21]([CH2:20]/[CH:19]=[CH:18]/[C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)[CH3:22])(=[O:9])=[O:8])=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 20655737(2S)-(4E)-5-(3-Pyridyl)-4-penten-2-ol

생성물 1

HCID 87465994(2S)-(4E)-5-(3-pyridyl)-4-penten-2-ol p-toluenesulfonate수율 68.6%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

Under a nitrogen atmosphere, p-toluenesulfonyl chloride (7.01 g, 36.77 mmol) was added to a stirring solution of (2S)-(4E)-5-(3-pyridyl)-4-penten-2-ol (3.00 g, 18.38 mmol) in dry triethylamine (20 mL) at 0° C. After stirring and warming to ambient temperature over 18 h, the mixture was stirred with cold, saturated NaHCO3 solution (50 mL) for 1 hour and extracted with chloroform (3×50 mL). The combined chloroform extracts were dried (K2CO3), filtered, and concentrated by rotary evaporation to afford a thick, dark-brown mass (˜7 g). The crude product was purified by column chromatography on silica gel, eluting with chloroform-acetone (98:2, v/v) to afford 4.00 g (68.6%) of a light-brown syrup.

후처리

  1. extractionextracted with chloroform (3×50 mL)
  2. dry with materialThe combined chloroform extracts were dried (K2CO3)
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. customto afford a thick, dark-brown mass (˜7 g)
  6. customThe crude product was purified by column chromatography on silica gel
  7. washeluting with chloroform-acetone (98:2

출처 및 근거

ORD 기록
ord-06fc4bb65cf04e6589d65c6b8e2f790d
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07045538B2

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