Methanol → Methyl 2-(benzyloxy)-5-(oxazol-5-yl)benzoate

HRID 454480Notes

Reaction equation

HRID 454480 reaction equation
C1(C)C=CC(S([CH2:10][N+:11]#[C-:12])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].CO.[CH2:22]([O:29][C:30]1[CH:45]=[CH:44][C:43]([CH:46]=[O:47])=[CH:42][C:31]=1[C:32]([O:34][CH2:35]C1C=CC=CC=1)=[O:33])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(OCC)(=O)C.O>[CH2:22]([O:29][C:30]1[CH:45]=[CH:44][C:43]([C:46]2[O:47][CH:12]=[N:11][CH:10]=2)=[CH:42][C:31]=1[C:32]([O:34][CH3:35])=[O:33])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium Carbonate2×HCID 161915Tosylmethyl isocyanide2×HCID 10405334Benzyl 2-benzyloxy-5-formylbenzoate

Product 1

HCID 66990185Methyl 2-(benzyloxy)-5-(oxazol-5-yl)benzoateYield 67.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

p-Toluenesulfonylmethyl isocyanide (0.55 g) and potassium carbonate (0.39 g) were added to a methanol (9 mL) suspension of the obtained benzyl 2-(benzyloxy)-5-formylbenzoate (0.93 g), followed by heating to reflux for 1 hour and 40 minutes. The reaction mixture was cooled to room temperature, and then p-toluenesulfonylmethyl isocyanide (0.079 g) and potassium carbonate (0.058 g) were added thereto, followed by heating to reflux for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 70-50% hexane/ethyl acetate] to obtain 0.56 g of methyl 2-(benzyloxy)-5-(oxazol-5-yl)benzoate as a light yellow solid.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 1 hour and 40 minutes
  3. temperatureby heating
  4. temperatureto reflux for 1 hour and 30 minutes
  5. temperatureThe reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. washwashed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography [eluent: 70-50% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-25740d227d5648338fd27c0557354a9d
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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