Ethyl Acetate → HCID 89975678, compound

HRID 716154Notes

Reaction equation

HRID 716154 reaction equation
[CH3:1][S:2]([O:5][CH:6]([CH:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:9][CH2:10][OH:11])[CH3:7])(=[O:4])=[O:3].C(OCC)(=O)C.C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][S:2]([O:5][CH:6]([CH:8]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:9][CH:10]=[O:11])[CH3:7])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 89975552HCID 89975552, compound

Product 1

HCID 89975678HCID 89975678, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.2 g of 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(H)-one (Dess-Martin Periodinane) was added to a solution of 490 mg of 5-hydroxy-3-phenylpentan-2-yl methanesulfonate in 5 mL of dichloromethane, and the obtained mixture was then stirred at room temperature for 2 hours. Thereafter, ethyl acetate and a saturated sodium hydrogen carbonate aqueous solution were added to the reaction mixture. The organic layer was fractionated, and it was successively washed with a sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, and the obtained residue was then purified by silica gel column chromatography (ethyl acetate/hexane=1/10 to 1/1), so as to obtain 414 mg of 5-oxo-3-phenylpentan-2-yl methanesulfonate in the form of a colorless oily product.

Workup

  1. washit was successively washed with a sodium thiosulfate aqueous solution
  2. dry with materiala saturated sodium chloride aqueous solution, and was then dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure
  4. customthe obtained residue was then purified by silica gel column chromatography (ethyl acetate/hexane=1/10 to 1/1)

Sources & evidence

ORD record
ord-6c68950e41084644b1718be1849bb6bc
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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