Potassium Carbonate → HCID 52450108, compound

HRID 1442572Notes

Reaction equation

HRID 1442572 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:10]([C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1)#[N:11].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:10]([C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])#[N:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 79177tert-Butyl bromoacetate

Product 1

HCID 52450108HCID 52450108, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl bromoacetate (9.01 g, 46 mmol) was dropwise added to a mixture of 3-cyanophenol (5.0 g, 42 mmol), potassium carbonate (13.82 g, 100 mmol) and DMF (40 ml) while stirring. After stirring for 8 hours, the mixture was poured onto ice water followed by extraction with ethyl ether. The extract was washed with saturated brine. After drying over anhydrous magnesium sulfate, the solvent was concentrated under reduced pressure. The residue was applied to column chromatography using silica gel (200 g) and eluted with hexane-ethyl acetate (3:1, v/v) to give the title compound (9.70 g, 99%) as an oily substance.

Workup

  1. stirringAfter stirring for 8 hours
  2. additionthe mixture was poured onto ice water
  3. extractionfollowed by extraction with ethyl ether
  4. washThe extract was washed with saturated brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. concentrationthe solvent was concentrated under reduced pressure
  7. washeluted with hexane-ethyl acetate (3:1

Sources & evidence

ORD record
ord-707ddf43c7f4442a83923200ff8e2c00
Source dataset
uspto-grants-2010_02
Patent number
US07659267B2

Reaction notes

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