Water → (1S)-1-propylheptyl p-toluenesulfonate

HRID 733491노트

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HRID 733491 반응식
[CH2:1]([C@@H:7]1[CH2:9][O:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:10]([Mg]Cl)[CH3:11].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1.O>O1CCCC1.[Cu](Cl)Cl.C(OCC)(=O)C.N1C=CC=CC=1>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([O:8][C@@H:7]([CH2:9][CH2:10][CH3:11])[CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])(=[O:22])=[O:21])=[CH:16][CH:15]=1

참가 물질

9

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 1620686(2R)-2-HexyloxiraneHCID 178461633HCID 178461633, 화합물

생성물 1

HCID 11565859(1S)-1-propylheptyl p-toluenesulfonate

시약·촉매·용매 4

HCID 24014Cupric Chloride촉매HCID 1049Pyridine용매HCID 8028Tetrahydrofuran용매3회HCID 8857Ethyl Acetate용매

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온도
-20 °C

실험 절차

(2R)-2-Hexyloxirane (1.22 mL, 100% ee) was added dropwise to a tetrahydrofuran (2.21 mL) solution of copper chloride (15.8 mg) at −20° C. under argon atmosphere, and then a 2.11 mol/L ethyl magnesium chloride in tetrahydrofuran solution (4.55 mL) was added dropwise thereto. The reaction mixture was stirred at −20° C. for 1.5 hours, and a tetrahydrofuran solution of p-toluenesulfonyl chloride (1.83 g) was added dropwise thereto, followed by stirring for 1.5 hours. Then, the temperature was raised up to 0° C., followed by stirring for 3.5 hours. To the reaction solution were added water and pyridine, followed by stirring at 0° C. for 40 minutes, ethyl acetate was added thereto and the mixture was successively washed with 10% sulfuric acid (twice), water and brine and concentrated to give the title compound (2.27 g) having the following physical data.

후처리

  1. stirringby stirring for 1.5 hours
  2. temperatureThen, the temperature was raised up to 0° C.
  3. stirringby stirring for 3.5 hours
  4. stirringby stirring at 0° C. for 40 minutes
  5. washthe mixture was successively washed with 10% sulfuric acid (twice), water and brine
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-45710ffc796440f0b95ffc1d85a00d0d
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589221B2

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