Sodium Carbonate → 2-(4-Thiophen-2-yl-phenyl)-5-methyl-4-oxazoleethanol

HRID 348276Notes

Reaction equation

HRID 348276 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:16])=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=2)=[CH:4][CH:3]=1.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:16])=[C:11]([CH2:13][CH2:14][OH:15])[N:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27339602-Thiopheneboronic acidHCID 108805302-(2-(4-Bromophenyl)-5-methyloxazol-4-YL)ethanol

Product 1

HCID 210842832-(4-Thiophen-2-yl-phenyl)-5-methyl-4-oxazoleethanol

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

2-(4-Bromophenyl)-5-methyl-4-oxazoleethanol (10.0 g, 35.0 mmol) (see Ex. 1, Part G) and 2-thiophenyl boronic acid (38.0 mmol) were dissolved in n-propanol (120 ml) before adding triphenylphosphine (165.2 mg, 0.63 mmol), palladium acetate (46 mg, 2.1 mmol), and Na2CO3 (4.5 g, 42 mmol dissolved in 30 mL distilled H2O). The solution was heated to reflux and stirred for 1.5 h. After cooling to ambient temperature, the mixture was concentrated under reduced pressure and then partitioned between CH2Cl2 (100 mL) and 1N NaOH (100 mL). The aqueous phase was extracted with CH2Cl2 (2×50 mL) and the combined organic phases were dried (MgSO4) and concentrated under reduced pressure to provide 2-(4-thiophen-2-yl-phenyl)-5-methyl-4-oxazoleethanol.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. concentrationthe mixture was concentrated under reduced pressure
  4. custompartitioned between CH2Cl2 (100 mL) and 1N NaOH (100 mL)
  5. extractionThe aqueous phase was extracted with CH2Cl2 (2×50 mL)
  6. dry with materialthe combined organic phases were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0e73865833f949b8aab027a622d371b5
Source dataset
uspto-grants-2007_02
Patent number
US07176224B2

Reaction notes

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