Potassium Carbonate → Methyl 4-(1,3-oxazol-5-yl)benzoate

HRID 2228594Notes

Reaction equation

HRID 2228594 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=[O:2].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(S([CH2:28][N+:29]#[C-:30])(=O)=O)=CC=1>CO>[O:2]1[C:1]([C:3]2[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=2)=[CH:30][N:29]=[CH:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15294Methyl 4-FormylbenzoateHCID 161915Tosylmethyl isocyanide

Product 1

HCID 1477779Methyl 4-(1,3-oxazol-5-yl)benzoateYield 79.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-formylbenzoate (Aldrich Chemical Co., St Louis, Mo.) (5.0 g, 30.5 mmol), anhydrous potassium carbonate (4.55 g, 33 mmol) and p-toluenesulfonylmethyl isocyanide (TOSMIC, Aldrich Chemical Co.) (6.83 g, 30.5 mmol) were refluxed in methanol (100 ml) for 3.5 hours. The mixture was then concentrated to dryness in vacuo. The residue was dissolved in ethyl acetate, washed twice with water, dried and concentrated in vacuo to give methyl 4-(1,3-oxazol-5-yl)benzoate as a beige solid (4.95 g). (NMR (300 MHz, CDCl3: 8.10 (d, 2H), 7.98 (s, 1H), 7.75 (d, 2H), 7.48 (s, 1H), 3.94 (s, 3H)).

Workup

  1. concentrationThe mixture was then concentrated to dryness in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed twice with water
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-556ee265a28b4f47841c9a86afb42f2d
Source dataset
uspto-grants-2002_07
Patent number
US06417185B1

Reaction notes

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