Sodium Hydroxide → HCID 11386089, compound

HRID 2106436Notes

Reaction equation

HRID 2106436 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]4([C:31]([CH3:34])([CH3:33])[CH3:32])[O:30][CH2:29][CH2:28][O:27]4)=[C:20]([CH3:35])[CH:19]=3)([CH2:16][CH3:17])[CH2:14][CH3:15])=[CH:10][C:9]=2[CH:36]=1)=[O:4].[OH-].[Na+]>CO.C1COCC1>[C:31]([C:26]1([CH2:25][O:24][C:21]2[CH:22]=[CH:23][C:18]([C:13]([C:11]3[O:12][C:8]4[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:36][C:9]=4[CH:10]=3)([CH2:14][CH3:15])[CH2:16][CH3:17])=[CH:19][C:20]=2[CH3:35])[O:30][CH2:29][CH2:28][O:27]1)([CH3:32])([CH3:33])[CH3:34]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 11214092HCID 11214092, compound

Product 1

HCID 11386089HCID 11386089, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-{1-[4-(2-tert-butyl-[1,3]dioxolan-2-ylmethoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzofuran-5-carboxylic acid methyl ester (1.51 g, 3.05 mmol) in methanol (5.0 mL) and THF (5.0 mL) and is treated with NaOH (2.0 M, 10 mL). The resulting mixture is stirred at RT for 2 h. The mixture is concentrated and neutralized with HCl (1 N) till pH˜3, and extracted with EtOAc (3×50 mL). The organic layer is dried over Na2SO4, concentrated to afford the title compound (1.43 g, 95%).

Workup

  1. concentrationThe mixture is concentrated
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-50a6a6835a624846b1f3301bcb872b64
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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