Ethyl Acetate → HCID 89975552, compound

HRID 716153Notes

Reaction equation

HRID 716153 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:13][S:14]([O:17][CH:18]([CH:20]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:21][CH2:22][O:23][Si](C(C)C)(C(C)C)C(C)C)[CH3:19])(=[O:16])=[O:15].C(OCC)(=O)C.C(=O)([O-])O.[Na+]>CO>[CH3:13][S:14]([O:17][CH:18]([CH:20]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:21][CH2:22][OH:23])[CH3:19])(=[O:16])=[O:15]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 123578460HCID 123578460, compound

Product 1

HCID 89975552HCID 89975552, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.24 g of p-toluenesulfonic acid monohydrate was added to a solution of 1.05 g of 3-phenyl-5-((tris(propan-2-yl)silyl)oxy)pentan-2-yl methanesulfonate in 15 mL of methanol, and the obtained mixture was then stirred at room temperature for 1 hour. 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 water 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=1/4 to 1/1), so as to obtain 0.56 g of 5-hydroxy-3-phenylpentan-2-yl methanesulfonate in the form of a colorless oily product.

Workup

  1. washit was successively washed with water
  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=1/4 to 1/1)

Sources & evidence

ORD record
ord-898d3121777b4dbdb72a552a6adce37e
Source dataset
uspto-grants-2015_11
Patent number
US09187514B2

Reaction notes

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