Potassium Carbonate → HCID 22503082, compound

HRID 1814474Notes

Reaction equation

HRID 1814474 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH:2]=[CH2:3].Br[CH2:12][C:13](OC)=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:12][CH2:13][OH:14])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 156242-AllylphenolHCID 60984Methyl bromoacetate

Product 1

HCID 22503082HCID 22503082, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Allylphenol (5.066 g) was dissolved in N,N-dimethylformamide (70 ml), followed by the addition of methyl 2-bromoacetate (6.931 g) and potassium carbonate (7.88 g), and the resulting mixture was stirred at 100° C. overnight. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was dissolved in tetrahydrofuran (40 ml), followed by the addition of lithium aluminium hydride (1.442 g) in small portions under ice-cooling. The resulting mixture was stirred for 5 min. To the reaction mixture were sequentially added water (1.5 ml), 5N sodium hydroxide (1.5 ml) and water (4.5 ml), and the resulting insoluble matters were filtered off through Celite. The resulting filtrate was partitioned between ethyl acetate and water. The organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by (NH) silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a colorless oil (5.248 mg, yield; 76%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water
  3. dry with materialdried (over MgSO4)
  4. customevaporated
  5. dissolutionThe resulting residue was dissolved in tetrahydrofuran (40 ml)
  6. additionfollowed by the addition of lithium aluminium hydride (1.442 g) in small portions under ice-
  7. temperaturecooling
  8. stirringThe resulting mixture was stirred for 5 min
  9. filtrationthe resulting insoluble matters were filtered off through Celite
  10. customThe resulting filtrate was partitioned between ethyl acetate and water
  11. washThe organic layer was washed with water
  12. dry with materialdried (over MgSO4)
  13. customevaporated
  14. customThe resulting residue was purified by (NH) silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-7f23d387f78a4777ac8468c78bf2099f
Source dataset
uspto-grants-2005_04
Patent number
US06875761B2

Reaction notes

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