Ethyl Acetate → Ethyl 2-phenyl-1,3-oxazole-4-carboxylate

HRID 2236172Notes

Reaction equation

HRID 2236172 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([O:12][C:13]([C:15]1[N:16]=[C:17](Cl)[O:18][CH:19]=1)=[O:14])[CH3:11].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>COCCOC.CCCCCC>[CH2:10]([O:12][C:13]([C:15]1[N:16]=[C:17]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[O:18][CH:19]=1)=[O:14])[CH3:11]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 2763184Ethyl 2-chlorooxazole-4-carboxylate

Product 1

HCID 571056Ethyl 2-phenyl-1,3-oxazole-4-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of phenylboronic acid (729 mg, 5.98 mmol), 2-chloro-oxazole-4-carboxylic acid ethyl ester (prepared according to the procedures described in Org. Lett. 2002, 4 (17), 2905 and J. Med. Chem. 1971, 14, 1075) (1.0 g, 5.70 mmol), Pd[PPh3]4 (329 mg, 0.285 mmol), and sodium carbonate (2M, 2 mL) in ethylene glycol dimethyl ether (10 mL) were heated at 90 degrees overnight. After cooling the reaction, solvent was removed to give the crude residue. Flash chromatography (Merck silica gel 60, 230-400 mesh, 5-45% ethyl acetate in hexane for 35 min) gave 2-phenyl-oxazole-4-carboxylic acid ethyl ester (1.03 g, 83%) as colorless oil. LCMS calcd for C12H11NO3 (m/e) 217, obsd 218 (M+H).

Workup

  1. customprepared
  2. temperatureAfter cooling
  3. customthe reaction, solvent
  4. customwas removed
  5. customto give the crude residue

Sources & evidence

ORD record
ord-2c5fc3e908824dc3a1fc5e57e327d6a1
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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