Potassium Carbonate → 4-(4-(2-Oxazolyl)phenoxy)benzaldehyde

HRID 630308Notes

Reaction equation

HRID 630308 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C([O-])([O-])=O.[K+].[K+].F[C:20]1[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:20]2[CH:27]=[CH:26][C:23]([CH:24]=[O:25])=[CH:22][CH:21]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 516892Sodium BicarbonateHCID 1356214594-(Oxazol-2-yl)phenol

Product 1

HCID 866134384-(4-(2-Oxazolyl)phenoxy)benzaldehydeYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(2-oxazolyl)phenol (4.1 g, 25.44 mmol) in DMF (98 ml), K2CO3 (3.52 g, 25.44 mmol, 1 equiv.) was added. The reaction was stirred at ambient temperature for 30 min. Then, 4-fluorobenzaldehyde (2.73 mL, 25.44 mmol, 1 equiv., Aldrich #12, 837-6) was added and stirring was continued at 150 C for 4 hours. After cooling, saturated NaHCO3 was added to the reaction mixture. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Flashmaster chromatography on 50 g of silica gel using a gradient of 100% hexane→50% hexane+50% ethyl acetate gave 6.4 g of 4-[4-(2-oxazolyl)phenoxy]benzaldehyde still containing 20 mol % DMF. Further drying led to the pure product (6.05 g; 90% th.; 148% pract.); 1H NMR (CDCl3) δ 9.95 (s, 1H), 8.09 (d, 2H), 7.89 (d, 2H), 7.72 (d, 1H), 7.24 (d, 1H), 7.16 (d, 2H), 7.13 (d, 2H) ppm.

Workup

  1. stirringstirring
  2. waitwas continued at 150 C for 4 hours
  3. temperatureAfter cooling
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3bf22c0dc415447da77b9b5246d51c21
Source dataset
uspto-grants-2016_04
Patent number
US09315509B2

Reaction notes

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