Sodium Hydroxide → HCID 68817136, compound

HRID 2106428Notes

Reaction equation

HRID 2106428 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]([CH3:32])[CH:19]=3)[CH3:17])[CH2:14][CH3:15])=[CH:10][C:9]=2[CH:33]=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:33][C:9]=3[CH:10]=2)[CH2:14][CH3:15])[CH3:17])=[CH:19][C:20]=1[CH3:32]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68813225HCID 68813225, compound

Product 1

HCID 68817136HCID 68817136, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-ethylpropyl}-benzofuran-5-carboxylic acid methyl ester (5.30 g, 11.8 μmmol) in methanol (30.0 mL) and THF (30.0 mL) is treated with NaOH (2.0 M, 60 mL). The resulting mixture is stirred at RT for 16 h. The mixture is concentrated and neutralized with HCl (5 N) till pH˜3, and extracted with EtOAc (2×100 mL). The organic layer is dried over Na2SO4, concentrated to afford the title compound (4.85 g, 94%).

Workup

  1. concentrationThe mixture is concentrated
  2. extractionextracted with EtOAc (2×100 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5c91d1fb085b4facb230a94ed98fadbd
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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