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

HRID 733491ノート

反応式

HRID 733491 の反応式
[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

参加物

9

反応物 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 1620686(2R)-2-HexyloxiraneHCID 178461633HCID 178461633、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 24014Cupric Chloride触媒HCID 1049Pyridine溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-20 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-45710ffc796440f0b95ffc1d85a00d0d
出典データセット
uspto-grants-2009_09
特許番号
US07589221B2

反応ノート

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