Potassium Carbonate → HCID 18512249, compound

HRID 1370838Notes

Reaction equation

HRID 1370838 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([OH:12])[CH:8]=[CH:9][C:10]=1[Br:11])[CH:2]=[CH2:3].[C:13]([O-:16])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)C>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][C:10]=1[Br:11])[O:12][C:5]1[CH:6]=[CH:7][C:8]([CH:13]=[O:16])=[CH:9][CH:10]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 18512325HCID 18512325, compound

Product 1

HCID 18512249HCID 18512249, compoundYield 166.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Flurorbenzaldehyde (1.15 mL, 10.76 mmoles) was added to a solution of the product from Example 63B (1.76 g, 7.69 mmoles) and K2CO3 (3.19 g, 23.1 mmoles) in DMF (7.7 mL). The reaction mixture was heated to 100° C. for 14 h and was cooled to room temperature The crude products were diluted with diethyl ether, extracted with sat. NH4Cl, extracted with H2O (2×), rinsed with brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography on a prepacked Biotage colum (hexane to 4:1 hexane:ethyl acetate) on silica gel to provide the title compound (2.13 g, 83%) as a white solid.

Workup

  1. extractionextracted with sat. NH4Cl
  2. extractionextracted with H2O (2×)
  3. washrinsed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on a prepacked Biotage colum (hexane to 4:1 hexane:ethyl acetate) on silica gel

Sources & evidence

ORD record
ord-e7e19442ea20464682ca88450b8b7a45
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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