Sodium Hydroxide → HCID 68813591, compound

HRID 2106440Notes

Reaction equation

HRID 2106440 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]([CH:32]([CH3:34])[CH3:33])[CH:19]=3)[CH3:17])[CH2:14][CH3:15])=[CH:10][C:9]=2[CH:35]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1>[CH3:30][C:27]([CH3:28])([CH3:29])[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:35][C:9]=3[CH:10]=2)[CH2:14][CH3:15])[CH3:17])=[CH:19][C:20]=1[CH:32]([CH3:33])[CH3:34]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68813539HCID 68813539, compound

Product 1

HCID 68813591HCID 68813591, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-isopropyl-phenyl]-ethylpropyl}-benzofuran-5-carboxylic acid methyl ester (1.55 g, 3.24 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) till pH˜3, and extracted with EtOAc (3×30 mL). The organic layer is dried over Na2SO4, concentrated to afford the title compound (1.49 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-8347b81095da4f5c987aa8ac6ee27990
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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