Dimethylformamide → 2-Phenyl-1,3-oxazole-5-carbaldehyde

HRID 868912Notes

Reaction equation

HRID 868912 reaction equation
O=P(Cl)(Cl)Cl.[C:6]1([C:12]2[O:13][CH:14]=[CH:15][N:16]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+].CN([CH:22]=[O:23])C>>[C:6]1([C:12]2[O:13][C:14]([CH:22]=[O:23])=[CH:15][N:16]=2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 5892802-Phenyl-1,3-oxazole

Product 1

HCID 132830212-Phenyl-1,3-oxazole-5-carbaldehyde

Conditions

Temperature
100 °C

Procedure

To a 50 mL flask charged with DMF (5 mL) was added POCl3 (0.7 g, 4.6 mmol) dropwise at 0° C. After stirring for 10 min, a solution of 2-phenyloxazole (0.6 g, 4.1 mmol) in DMF (5 mL) was added dropwise. The reaction mixture was heated to 100° C. and stirred for 48 h. After cooling to room temperature, the reaction mixture was poured into ice water and the pH was adjusted to 10 with 10% aqueous NaOH. The aqueous mixture was extracted with EtOAc (20 mL×3). The combined organic layers were dried over Na2SO4 and filtered. The filtrate was concentrated and purified by column chromatography to give 240 mg of the desired product. LC-MS: m/z 174 (M+H+).

Workup

  1. stirringstirred for 48 h
  2. temperatureAfter cooling to room temperature
  3. extractionThe aqueous mixture was extracted with EtOAc (20 mL×3)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-6585e451f7dd4eb888981db696695791
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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