Phenol → HCID 23590026, compound

HRID 1609934Notes

Reaction equation

HRID 1609934 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:40]1([OH:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C1(C)C=CC=CC=1.CCOCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[CH2:1]([O:3][C:4](=[O:31])[C:5]([CH3:7])([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([O:46][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)[CH3:6])[CH3:2]

Participants

8

Reactant 3

HCID 996PhenolHCID 62657Potassium Phosphate, TribasicHCID 110273422-(4-{2-[2-(4-Bromophenyl)-5-methyloxazol-4-yl]ethoxy}phenoxy)-2-methylpropionic acid ethyl ester

Product 1

HCID 23590026HCID 23590026, compoundYield 102.6%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 27342152-(Di-tert-butylphosphino)biphenylCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-(4-{2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-phenoxy)-2-methyl-propionic acid ethyl ester (0.30 g, 0.614 mmol), potassium phosphate (0.26 g, 1.22 mmol), 2-(di-tert-butylphosphino)biphenyl (0.014 g, 0.0469 mmol) and phenol (0.069 g, 0.733 mmol) in toluene (6 mL) was degassed three times by successive application of vacuum to the reaction vessel followed by nitrogen purge. Palladium (II) acetate (0.007 g, 0.0312 mmol) was added to the reaction and the mixture heated to reflux under nitrogen for 3 h. The reaction was cooled to room temperature, diluted with Et2O, and extracted with water then 1 N NaOH (10 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo to give 0.316 g of crude 2-methyl-2-(4-{2-[5-methyl-2-(4-phenoxy-phenyl)-oxazol-4-yl]-ethoxy}-phenoxy)-propionic acid ethyl ester

Workup

  1. customwas degassed three times by successive application of vacuum to the reaction vessel
  2. custompurge
  3. temperaturethe mixture heated
  4. temperatureto reflux under nitrogen for 3 h
  5. extractionextracted with water
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-aa5516f9e14840fda740b02a81e30a3d
Source dataset
uspto-grants-2006_01
Patent number
US06982278B2

Reaction notes

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