Water → HCID 57007664, compound

HRID 2289369Notes

Reaction equation

HRID 2289369 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][C@@H:12]2[O:14][CH2:13]2)(=[O:9])=[O:8])=[CH:3][CH:2]=1.O>C1COCC1.[Cu](Cl)(Cl)(Cl)Cl.[Li]>[C:1]1([CH3:15])[CH:6]=[CH:5][C:4]([S:7]([O:10][CH2:11][C@H:12]([OH:14])[CH2:13][CH2:3][CH2:2][C@@H:1]([CH3:15])[CH2:6][CH3:5])(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 962WaterHCID 154187Glycidyl tosylate, (R)-

Product 1

HCID 57007664HCID 57007664, compoundYield 206.9%

Reagents, catalysts & solvents 2

HCID 178478939HCID 178478939, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

Separately, 0.42 g of lithium copper tetrachloride was dissolved in 80 ml of THF in a flask, and the solution was cooled to -50° C. The above prepared Grignard reagent was added dropwise to the solution at that temperature, followed by stirring for 15 minutes. After cooling the reaction mixture to -55° C., a mixture of 2.0 g of (R)-glycidyl p-toluenesulfonate and 20 ml of THF was added thereto dropwise to conduct reaction at that temperature for 1.5 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and concentrated to obtain 2.85 g (25.64%) of the titled compound.

Workup

  1. additionwas added dropwise to the solution at that temperature
  2. temperatureAfter cooling the reaction mixture to -55° C.
  3. additionwas added
  4. customreaction at that temperature for 1.5 hours
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b292a943eb554076baf206e8588a3b9f
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

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