Phenol → HCID 10679746, compound

HRID 619831Notes

Reaction equation

HRID 619831 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:7]1([OH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:14]([O-])([O-])=O.[K+].[K+].[CH3:20][N:21](C=O)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>[CH3:6][O:5][C:3](=[O:4])[CH2:2][O:13][C:7]1[CH:12]=[CH:11][C:10]([C:20]#[N:21])=[CH:9][C:8]=1[CH3:14]

Participants

7

Reactant 4

HCID 996PhenolHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Product 1

HCID 10679746HCID 10679746, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Methyl bromoacetate (0.56 mL, 5.92 mmol) is added to a solution of phenol (0.70 g, 5.29 mmol), K2CO3 (1.6 g, 11.6 mmol) and tetrabutyl ammonium iodide (0.57 g, 1.53 mmol) in 30 mL of DMF. The resulting solution is heated to 80° C. for 16 hours. The solution is then cooled to ambient temperatures. The solution is diluted with EtOAc. The resulting solution is washed with H2O and saturated NaCl. The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 10% EtOAc/hexanes to 50% EtOAc/hexanes to afford the title compound (1.4 g, 0.8 mmol).

Workup

  1. temperatureThe solution is then cooled to ambient temperatures
  2. washThe resulting solution is washed with H2O and saturated NaCl
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by column chromatography
  7. washeluting with a gradient of 10% EtOAc/hexanes to 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-dc2e1ec6c62a40a1a9269904fa09f310
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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