Sodium Hydroxide → HCID 11259190, compound

HRID 2106429Notes

Reaction equation

HRID 2106429 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([CH2:31][CH3:32])([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]([OH:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[C:18]([CH3:30])[CH:17]=3)[CH2:14][CH3:15])=[CH:10][C:9]=2[CH:33]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1>[CH2:14]([C:13]([C:11]1[O:12][C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:33][C:9]=2[CH:10]=1)([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH:24]([OH:29])[C:25]([CH3:27])([CH3:28])[CH3:26])=[C:18]([CH3:30])[CH:17]=1)[CH2:31][CH3:32])[CH3:15]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11775341HCID 11775341, compound

Product 1

HCID 11259190HCID 11259190, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{1-ethyl-1-[4-(2-hydroxy-3,3-dimethyl-butoxy)-3-methyl-phenyl]-propyl}-benzofuran-5-carboxylic acid methyl ester (555 mg, 1.226 mmol) in methanol (3.0 mL) and THF (3.0 mL) and is treated with NaOH (2.0 M, 6.0 mL). The resulting mixture is stirred at RT for 18 h. The mixture is concentrated and neutralized with HCl (1 N) till pH˜2, and extracted with EtOAc (3×10 mL). The organic layer is dried over Na2SO4, concentrated to afford the title compound (530 mg, 99%).

Workup

  1. concentrationThe mixture is concentrated
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-72fbf0c8c6034dd797a9353bdc4986d0
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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