Cesium carbonate → HCID 69891893, compound

HRID 353232Notes

Reaction equation

HRID 353232 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:17](Br)[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[CH2:17]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 160545-HydroxyindoleHCID 98116Bromomethylstyrene

Product 1

HCID 69891893HCID 69891893, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-hydroxyindole (0.25 g) in acetonitrile (10 mL) was added cesium carbonate (1.22 g) and cinnamyl bromide (0.37 g). The suspension was stirred under nitrogen at ambient temperature overnight. Cesium salts were removed by filtration and washed with acetone. The residue left on concentrating the combined filtrate and washings was chromatographed over silica eel with a mixture of ethyl acetate and hexanes and crystallized from ether with hexanes to give 0.23 g of the title compound. MS CI (MH+)=250

Workup

  1. customCesium salts were removed by filtration
  2. washwashed with acetone
  3. waitThe residue left
  4. concentrationon concentrating the combined filtrate and washings
  5. customwas chromatographed over silica eel with a mixture of ethyl acetate and hexanes
  6. customcrystallized from ether with hexanes

Sources & evidence

ORD record
ord-81653e394f3240999101125623fa3b95
Source dataset
uspto-grants-2004_06
Patent number
US06750242B1

Reaction notes

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