Lithium Hydroxide → 2-[2-(4-{2-[Benzyl(ethyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acid

HRID 898914Notes

Reaction equation

HRID 898914 reaction equation
[CH2:1]([N:8]([CH2:32][CH3:33])[C:9](=[O:31])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][O:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([O:25]C)=[O:24])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[CH2:1]([N:8]([CH2:32][CH3:33])[C:9](=[O:31])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][O:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([OH:25])=[O:24])=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69259262Methyl 2-[2-(4-{2-[benzyl(ethyl)amino)-2-oxoethoxy}phenyl)ethoxy]benzoate

Product 1

HCID 692583742-[2-(4-{2-[Benzyl(ethyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acidYield 109.3%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 2-[2-(4-{2-[benzyl(ethyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoate (0.138 g, 0.308 mmol) was dissolved in a mixture of THF/water (1/1, 4 ml). Lithium hydroxide (0.015 g, 0.617 mmol) was added. The reaction was performed in an single node microwave oven (14 min, 150 deg). Workup by removing the solvent by evaporation and addition of HCl (2 ml, 1 M). The waterphase was extracted with two portions of EtOAc (20 ml), the organic phase was dried (MgSO4) and the solvent was removed by evaporation to give 0.146 g of 2-[2-(4-{2-[benzyl(ethyl)amino]-2-oxoethoxy}phenyl)ethoxy]benzoic acid.

Workup

  1. customThe reaction was performed in an single node microwave oven
  2. custom(14 min, 150 deg)
  3. customWorkup by removing the solvent
  4. customby evaporation and addition of HCl (2 ml, 1 M)
  5. extractionThe waterphase was extracted with two portions of EtOAc (20 ml)
  6. dry with materialthe organic phase was dried (MgSO4)
  7. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-fa9d2cc08b59463cb14913cac9ff1996
Source dataset
uspto-grants-2008_04
Patent number
US07351858B2

Reaction notes

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