Hexane → HCID 86633032, compound

HRID 558057Notes

Reaction equation

HRID 558057 reaction equation
[C:1]([O:6][CH:7]([O:11][C:12]([CH3:14])=[S:13])[CH:8]([CH3:10])[CH3:9])(=[O:5])[CH2:2][CH2:3][CH3:4].CCCCCC>CC(OC)(C)C.O>[C:1]([O:6][C@@H:7]([O:11][C:12]([CH3:14])=[S:13])[CH:8]([CH3:10])[CH3:9])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 8058HexaneHCID 86633030HCID 86633030, compound

Product 1

HCID 86633032HCID 86633032, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

2-Methyl-1-methylthiocarbonyloxypropyl butanoate (2d) (1 g) was dissolved in 20 mL of MTBE, saturated with 1% of water, 1.3 g of PLE/MPEG (7.5% , 60 mg/1 g) was added, and the mixture shaken at room temperature for 24 hrs. Hexane was added to the reaction mixture and after filtration through a CELITE® 545 pad, the organic solution was washed with water, aqueous sodium bicarbonate (NaHCO3) and brine, and dried over anhydrous sodium sulfate (Na2SO4). After evaporating the solvent under reduced pressure the title compound (14) was obtained (0.29 g, 58% yield). The absolute configuration was determined by derivatization to a compound having known stereochemistry.

Workup

  1. additionwas added
  2. filtrationafter filtration through a CELITE® 545 pad
  3. washthe organic solution was washed with water, aqueous sodium bicarbonate (NaHCO3) and brine
  4. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
  5. customAfter evaporating the solvent under reduced pressure the title compound (14)
  6. customwas obtained (0.29 g, 58% yield)

Sources & evidence

ORD record
ord-c79ef540ddb84e79b0279653294ca555
Source dataset
uspto-grants-2011_11
Patent number
US08062870B2

Reaction notes

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