Nitrogen → Ethyl 2-acetyloxazole-4-carboxylate

HRID 2040050Notes

Reaction equation

HRID 2040050 reaction equation
N#N.C1(/[CH:9]=[C:10](/[C:12]2[O:13][CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=2)\C)C=CC=CC=1.[OH2:22]>CC(C)=O>[C:10]([C:12]1[O:13][CH:14]=[C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:16]=1)(=[O:22])[CH3:9]

Participants

5

Reactant 3

HCID 947NitrogenHCID 962WaterHCID 66819964(E)-ethyl 2-(1-phenylprop-1-en-2-yl)oxazole-4-carboxylate

Product 1

HCID 66820192Ethyl 2-acetyloxazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of NalO4 (23 g, 108 mmol) in water (150) mL was slowly added to a vigorously stirred suspension of silica gel (110 g) in acetone (500 mL). The mixture was then concentrated under reduced pressure and the lumpy solid slurried in CH2Cl2 and the solvent was evaporated under reduced pressure. CH2Cl2 (500 mL) was added and the reaction mixture was treated at rt with (E)-ethyl 2-(1-phenylprop-1-en-2-yl)oxazole-4-carboxylate (8.3 g, 32.5 mmol) and RuC1-3 hydrate (550 mg, 1.0 mmol). The reaction mixture was stirred at rt in the dark for 60 min, filtered and concentrated under reduced pressure. Purification of the residue by FC (1:0→1:5 petroleum ether: Et2O) gave the title compound as a yellow solid. TLC:rf (1:1 EA-Hept)=0.52.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customthe lumpy solid slurried in CH2Cl2 and the solvent was evaporated under reduced pressure
  3. additionCH2Cl2 (500 mL) was added
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by FC (1:0→1:5 petroleum ether: Et2O)

Sources & evidence

ORD record
ord-63ad028ee87b4fc1b6c5b99fc9e89d3e
Source dataset
uspto-grants-2013_11
Patent number
US08580831B2

Reaction notes

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