Cesium carbonate → HCID 86617330, compound

HRID 661745Notes

Reaction equation

HRID 661745 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:10]=[CH:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:32](P(C(C)(C)C)C(C)(C)C)(C)(C)[CH3:33].C([Sn](CCCC)(CCCC)C=C)CCC>O1CCOCC1>[CH:32]([C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:10]=[CH:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1)=[CH2:33]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 81998TributylvinyltinHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 86617331HCID 86617331, compound

Product 1

HCID 86617330HCID 86617330, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

Phenyl N-(4-iodophenyl)-3-(phenoxy)acrylimidate (0.50 g), bis(benzylideneacetone)palladium (0) (0.023 g) and cesium carbonate (0.82 g) were suspended to dioxane (15 ml). Tri-t-butylphosphine (10 wt % in hexane: 0.24 g) and tributyl (vinyl) tin (0.44 g) were added thereto and it was stirred for four hours at room temperature and 60° C. for five hours. The unsolved matter was filtered off, and the filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain phenyl N-(4-vinylphenyl)-3-(phenoxy)acrylimidate (0.29 g) as yellow oil.

Workup

  1. filtrationThe unsolved matter was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was separated
  4. custompurified by silica gel column chromatography (hexane:ethyl acetate=30:1)

Sources & evidence

ORD record
ord-643bb31589e748cf9bd0a1e0577c6b99
Source dataset
uspto-grants-2011_12
Patent number
US08084644B2

Reaction notes

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