5-Isoxazolecarboxylic acid, 4-(dimethoxymethyl)-3-phenyl-, methyl ester → HCID 58537213, compound

HRID 1804494Notes

Reaction equation

HRID 1804494 reaction equation
C[O:2][CH:3]([O:19]C)[C:4]1[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:6][O:7][C:8]=1[C:9]([O:11][CH3:12])=[O:10].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:12][O:11][C:9]([C:8]1[O:7][N:6]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]=1[C:3]([OH:19])=[O:2])=[O:10]

Participants

4

Reactant 2

HCID 109457375-Isoxazolecarboxylic acid, 4-(dimethoxymethyl)-3-phenyl-, methyl esterHCID 131709961Jones' reagent2×

Product 1

HCID 58537213HCID 58537213, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 4-(dimethoxymethyl)-3-phenylisoxazole-5-carboxylate, 12-B, (144 mg, 0.519 mmol) in acetone (3 mL) at rt was added Jones' Reagent (0.539 mL, 0.727 mmol) and the resulting mixture was allowed to stir at rt for 1 hr. Three additional aliquots of Jones' Reagent (0.539 mL, 0.727 mmol) were added portion wise over 1 hr and stirring was continued at rt for 2 hr. At this time, the reaction mixture was partitioned between EtOAc (30 mL) and 2% NaHSO3 solution (30 mL). The organic layer was washed with brine (20 mL), dried (MgSO4) and concentrated to afford 5-(methoxycarbonyl)-3-phenylisoxazole-4-carboxylic acid (108 mg, 0.437 mmol, 84% yield) as a light yellow solid. HPLC retention time=1.30 minutes (PHENOMENEX® Luna 4.6×30 mm S-5 ODS column) eluting with 10-90% aqueous methanol+0.1% TFA over a 2 minute gradient. MS: (M+H)=248.13. 1H NMR (400 MHz, chloroform-d) δ ppm 4.16 (s, 3H), 7.50 (m, 3H), 7.66 (dd, J=8.2, 1.4 Hz, 2H).

Workup

  1. stirringstirring
  2. waitwas continued at rt for 2 hr
  3. customAt this time, the reaction mixture was partitioned between EtOAc (30 mL) and 2% NaHSO3 solution (30 mL)
  4. washThe organic layer was washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4728a97efb074598bbecb3c4e8a2a870
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

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