Sodium Hydroxide → HCID 68815364, compound

HRID 2106434Notes

Reaction equation

HRID 2106434 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([CH:13]([CH:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[C:20]([CH2:32][CH3:33])[CH:19]=3)[CH3:17])[CH2:14][CH3:15])=[CH:10][C:9]=2[CH:34]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1>[CH3:29][C:27]([CH3:28])([CH3:30])[C:26](=[O:31])[CH2:25][O:24][C:21]1[CH:22]=[CH:23][C:18]([CH:16]([CH:13]([C:11]2[O:12][C:8]3[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:34][C:9]=3[CH:10]=2)[CH2:14][CH3:15])[CH3:17])=[CH:19][C:20]=1[CH2:32][CH3:33]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68815347HCID 68815347, compound

Product 1

HCID 68815364HCID 68815364, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-ethyl-phenyl]-ethylpropyl}-benzofuran-5-carboxylic acid methyl ester (1.64 g, 3.53 mmol) in methanol (5.0 mL) and THF (5.0 mL) is treated with NaOH (2.0 M, 10 mL). The resulting mixture is stirred at RT for 12 h. The mixture is concentrated and neutralized with HCl (5 N) until pH˜3, and extracted with EtOAc (3×30 mL). The organic layer is dried over Na2SO4, concentrated to afford the title compound (1.57 g, 99%).

Workup

  1. concentrationThe mixture is concentrated
  2. extractionextracted with EtOAc (3×30 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e0985ba7c2364288bf345b34838517d4
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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