Citric Acid → HCID 67342138, compound

HRID 1673416Notes

Reaction equation

HRID 1673416 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(N(CCCC)CCCC)CCC.[C:22]([NH:30][C:31]1[CH:43]=[C:42]([CH:44]=[CH2:45])[CH:41]=[CH:40][C:32]=1[C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.CN(C)C(=O)C>[C:22]([NH:30][C:31]1[CH:43]=[C:42](/[CH:44]=[CH:45]/[C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)[CH:41]=[CH:40][C:32]=1[C:33]([O:35][C:36]([CH3:38])([CH3:39])[CH3:37])=[O:34])(=[O:29])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 7622TributylamineHCID 108944-IodophenolHCID 67343635Tert-butyl 2-(benzamido)-4-vinylbenzoate

Product 1

HCID 67342138HCID 67342138, compoundYield 64.9%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

0.12 g of 4-iodophenol, 0.18 mL of tributylamine and 4.2 mg of palladium acetate were added do 2.4 mL of N,N-dimethylacetamide solution containing 0.12 g of tert-butyl 2-(benzamido)-4-vinylbenzoate sequentially at room temperature and stirred under nitrogen atmosphere at 110° C. for 6 hours. After the reaction mixture was cooled to room temperature, 10% citric acid aqueous solution and ethyl acetate were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=1:1] to obtain 0.10 g of tert-butyl 2-(benzamido)-4-((E)-2-(4-hydroxyphenyl)vinyl)benzoate as yellow solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. washafter washed with 10% citric acid aqueous solution
  5. customa saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane:ethyl acetate=1:1]

Sources & evidence

ORD record
ord-a5d03d9238174a85813931d3ff4eb88a
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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