Sodium Hydroxide → HCID 68489933, compound

HRID 1616570Notes

Reaction equation

HRID 1616570 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:25])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH:13]=1>CO>[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:14]1[CH:13]=[C:12]([CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]([OH:25])=[O:4])[O:16][N:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59167757HCID 59167757, compound

Product 1

HCID 68489933HCID 68489933, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 2 N sodium hydroxide (15 mL) to a solution of 7-[3-(2-methoxyphenyl)isoxazol-5-yl]heptanoic acid methyl ester (2.89 g, 8 mmol) in methanol (50 mL) at room temperature under nitrogen and stir for 3 hours. Remove the solvent under reduced pressure, dilute the residue with water (100 mL), and wash with methyl tert-butyl ether (100 mL). Acidify the mixture to pH 1 with 1 N HCl and extract with ethyl acetate (3×100 mL). Wash the combined organic extracts with water (100 mL) and brine (100), dry over sodium sulfate, and remove the solvent under reduced pressure to provide 7-[3-(2-methoxyphenyl)isoxazol-5-yl]heptanoic acid (2.41 g, 98%): APCI mass spectrum m/z 302 [C17H21INO4—H]−.

Workup

  1. customRemove the solvent under reduced pressure
  2. additiondilute the residue with water (100 mL)
  3. washwash with methyl tert-butyl ether (100 mL)
  4. extractionextract with ethyl acetate (3×100 mL)
  5. washWash the combined organic extracts with water (100 mL) and brine (100)
  6. dry with materialdry over sodium sulfate
  7. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-4247c56cbf2344ff8f8bd4085d6faed1
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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