Sodium Hydroxide → HCID 44547311, compound

HRID 516827Notes

Reaction equation

HRID 516827 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12](=[O:20])[CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH:9]=[CH:10][CH:11]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12](=[O:20])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66875279HCID 66875279, compound

Product 1

HCID 44547311HCID 44547311, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Ethyl 4-(3-(2,6-Dichlorobenzyloxy)phenyl)-4-oxobutanoate (Step B, 14.86 g, 39 mmol) in abs ethanol (100 ml) was treated with 1N NaOH (60 ml) at room temperature. The reaction mixture was stirred for 3 hours, or until all the starting material is gone, concentrated and diluted with chloroform and washed with 1M HCl to bring the pH to 3.5-4. The organic layer was washed with brine, dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol, 95:5 spiked with acetic acid) to give the title compound as white solid.

Workup

  1. concentrationconcentrated
  2. additiondiluted with chloroform
  3. washwashed with 1M HCl
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography on a silica gel column (chloroform:methanol, 95:5 spiked with acetic acid)

Sources & evidence

ORD record
ord-95c5979d7876409ba655b0db52511f0f
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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