Sodium Hydroxide → HCID 178524296, compound

HRID 1023862Notes

Reaction equation

HRID 1023862 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=2[O:8][CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([O:15]C)=[O:14])[N:3]=[CH:2]1.[OH-].[Na+]>CO>[NH:1]1[CH:5]=[C:4]([C:6]2[CH:24]=[CH:23][CH:22]=[CH:21][C:7]=2[O:8][CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=2[C:13]([OH:15])=[O:14])[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178497628HCID 178497628, compound

Product 1

HCID 178524296HCID 178524296, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Methyl 2-(2-(2-(1H-imidazol-4-yl)phenoxy)ethyl)benzoate (30 mg, 0.093 mmol) was dissolved in methanol (3 mL) and aqueous NaOH (2M, 0.47 mL, 0.931 mmol) was added. The reaction mixture was heated at 60° C. for 16 h and methanol was evaporated under reduced pressure. The aqueous solution was neutralized to pH 7 and the aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic layers were dried and concentrated. The crude product was purified by flash column chromatography to give the desired acid as a white solid (23 mg, 0.075 mmol, 79%). 1H NMR (CD3OD): 3.52 (t, 2H, J=6.4 Hz), 4.39 (t, 2H, J=6.4 Hz), 6.96 (t, 1H, J=7.4 Hz), 7.07 (d, 1H, J=8.4 Hz), 7.22 (t, 2H, J=7.8 Hz), 7.31 (d, 2H, J=6 Hz), 7.45 (s, 1H), 7.69-7.71 (m, 2H), 7.91 (d, 1H, J=4.8 Hz).

Workup

  1. custommethanol was evaporated under reduced pressure
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×20 mL)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-3cac0836b2bc410b853b3e1d1f502310
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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