Water → HCID 22103669, compound

HRID 1457211Notes

Reaction equation

HRID 1457211 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[CH:11][N:12]=2)=[CH:4][C:3]=1[OH:13].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[CH:11][N:12]=2)=[CH:4][C:3]=1[O:13][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 22103807HCID 22103807, compound

Product 1

HCID 22103669HCID 22103669, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the title compound of Step (A) (0.42 g, 1.75 mmol) in 5 mL of DMF at 50° C., anhydrous potassium carbonate (0.29 g, 2.09 mmol) and 1-bromo-3-phenyl propane (0.52 g, 2.63 mmol) were added and stirred for 15 hr. The mixture was then added to 25 mL water and the solution was extracted with 3×25 mL EtOAc. The combined organic extracts were washed with water and dried and evaporated. The residue thus obtained was chromatographed on 25 g of silica gel using 3:1 hexane:EtOAc to afford 0.32 g (51%) of the title compound of this step as a light yellow oil.

Workup

  1. extractionthe solution was extracted with 3×25 mL EtOAc
  2. washThe combined organic extracts were washed with water
  3. customdried
  4. customevaporated
  5. customThe residue thus obtained
  6. customwas chromatographed on 25 g of silica gel using 3:1 hexane

Sources & evidence

ORD record
ord-e776ebcf93064bfba0211e041a1fc026
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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