Sodium Hydroxide → HCID 67087716, compound

HRID 2175722Notes

Reaction equation

HRID 2175722 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])/[CH:6]=[CH:7]/[C:8]1[O:9][C:10]2[C:11](=[C:13]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:15][CH:16]=2)[N:12]=1.[OH-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])/[CH:6]=[CH:7]/[C:8]1[O:9][C:10]2[C:11](=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=[CH:15][CH:16]=2)[N:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67087851HCID 67087851, compound

Product 1

HCID 67087716HCID 67087716, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (E)-methyl 2-(3,4-dimethoxystyryl)benzo[d]oxazole-4-carboxylate (240 mg, 0.71 mmol) in THF (10 mL) and MeOH (5 mL) was added 2 N NaOH solution (1.77 mL) dropwise at room temperature. The resulting mixture was stirred at room temperature for two hours then quenched with a 1N HCl solution. The mixture was then extracted with DCM and the organic phase was washed with saturated aqueous NaCl solution and dried over sodium sulfate. The solvent was then removed under reduced pressure to give (E)-2-(3,4-Dimethoxystyryl)benzo[d]oxazole-4-carboxylic acid (170 mg, 74%). 1H-NMR (400 MHz, DMSO-d6) δ 3.81 (s, 3H), 3.85 (s, 3H), 7.03 (d, J=8.0 Hz, 1H), 7.33-7.39 (m, 2H), 7.46 (app t, J=8.0 Hz, 1H), 7.50 (d, J=2.0 Hz, 1H), 7.80 (d, J=16.0 Hz, 1H), 7.87 (dd, J=8.0, 1.2 Hz, 1H), 7.93 (dd, J=8.0, 1.2 Hz, 1H); LC-MS (ES-API): rt 8.88 min; m/z calculated for C18H15NO5 [M−H]− 324.1, found 324.1.

Workup

  1. customthen quenched with a 1N HCl solution
  2. extractionThe mixture was then extracted with DCM
  3. washthe organic phase was washed with saturated aqueous NaCl solution
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was then removed under reduced pressure

Sources & evidence

ORD record
ord-d6deca4a5bdd4af68867d46e9af21235
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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