Water → HCID 12742057, compound

HRID 878529Notes

Reaction equation

HRID 878529 reaction equation
[C:1]1([CH2:7][C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].[CH:12](OCC)=[O:13].O>C(OCC)C>[OH:13]/[CH:12]=[CH:9]/[C:8](=[O:10])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7678PhenylacetoneHCID 8025Ethyl formateHCID 5360545Sodium

Product 1

HCID 12742057HCID 12742057, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 1-phenylpropan-2-one (1.78 g, 13 mmol) in anhydrous diethyl ether (50 ml) containing sodium cut in small pieces (299 mg, 13 mmol), ethyl formate (1.4 g, 20 mmol) was added slowly with stirring and ice-cooling. After standing overnight at rt, water was added, and the ether layer was washed with water. The organic phase was dried, concentrated, and purified by flash column chromatography (PE/EtOAc=10:1) to give the title compound (1.2 g, 57%) as a yellow oil.

Workup

  1. additionwas added slowly
  2. temperatureice-cooling
  3. washthe ether layer was washed with water
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (PE/EtOAc=10:1)

Sources & evidence

ORD record
ord-6fa8062385c1472a95498c7ba8e2d72a
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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