Potassium Carbonate → HCID 57517511, compound

HRID 2368146Notes

Reaction equation

HRID 2368146 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CS(O[CH2:17][CH2:18][CH:19]1[CH2:21][CH2:20]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:19]1([CH2:18][CH2:17][O:8][C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=2)[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 162713-Nitro-p-cresolHCID 145578092-Cyclopropylethyl methanesulfonate

Product 1

HCID 57517511HCID 57517511, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 4-methyl-3-nitrophenol (3 g), 2-cyclopropylethyl methanesulfonate (3.22 g) and potassium carbonate (2.71 g) in DMF (100 mL) was stirred at 80° C. for 6 hr. The reaction mixture was allowed to cool to room temperature, and the solvent was evaporated under reduced pressure. The obtained residue was extracted with ethyl acetate and water, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (NH, hexane/ethyl acetate) to give the title compound (3.65 g).

Workup

  1. temperatureto cool to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. extractionThe obtained residue was extracted with ethyl acetate and water
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-665b16f1e96f4195bb16b850731e2a00
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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