Toluene → HCID 10886086, compound

HRID 584429Notes

Reaction equation

HRID 584429 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:14]/[O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[N:26]=[C:27]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[O:28][C:29]=3[CH3:30])=[CH:19][CH:18]=2)/[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.[C:37]1(/[CH:43]=[CH:44]/C2C=CC(B(O)O)=CC=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>O.C(O)C>[CH3:30][C:29]1[O:28][C:27]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[N:26][C:25]=1[CH2:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][O:15]/[N:14]=[C:8](/[C:5]2[CH:4]=[CH:3][C:2](/[CH:44]=[CH:43]/[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[CH:7][CH:6]=2)\[C:9]([OH:11])=[O:10])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 10896909HCID 10896909, compoundHCID 22344583HCID 22344583, compound

Product 1

HCID 10886086HCID 10886086, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of ethyl Z-2-(4-bromophenyl)-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]acetate (830 mg), 4-(E-2-phenylethenyl)phenylboronic acid (268 mg), potassium carbonate (626 mg), toluene (20 ml), ethanol (2 ml) and water (2 ml) was stirred under an argon atmosphere for 30 minutes at room temperature. Tetrakis (triphenylphosphine)palladium (0) (105 mg) was added and the mixture was heated under reflux for 14 hours. The reaction mixture was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residues were subjected to column chromatography on silica gel to obtain an oil from a fraction eluted with ethyl acetate-hexane (1:3, v/v). This oil was dissolved in tetrahydrofuran (10 ml)-methanol (5 ml), and 1N aqueous solution of sodium hydroxide (5 ml) was added and the mixture was stirred for 2 hours at 40° C. 1N HCl (5.5 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride, dried (MgSO4) and then concentrated. The residual crystal was recrystallized from ethyl acetate-hexane to obtain Z-2-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyloxyimino]-2-[4-(E-2-phenylethenyl)phenyl]acetic acid (634 mg, yield: 77%) as pale-yellow crystals. m.p. 194-195° C. (decomposition)

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 14 hours
  3. washThe reaction mixture was washed with saturated aqueous sodium chloride
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customto obtain an oil from a fraction
  7. washeluted with ethyl acetate-hexane (1:3
  8. dissolutionThis oil was dissolved in tetrahydrofuran (10 ml)-methanol (5 ml), and 1N aqueous solution of sodium hydroxide (5 ml)
  9. additionwas added
  10. stirringthe mixture was stirred for 2 hours at 40° C
  11. addition1N HCl (5.5 ml) was added to the reaction mixture
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated
  16. customThe residual crystal was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b6429c3802f54480b3c4a3819347984f
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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