Sodium Hydroxide → 2-Ethoxy-3-{4-[2-(9H-fluoren-9-yl)-ethoxy]-phenyl}-propionic acid

HRID 1841283Notes

Reaction equation

HRID 1841283 reaction equation
[OH-].[Na+].[CH2:3]([O:5][CH:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH:22]2[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:15][CH:14]=1)[C:7]([O:9]CC)=[O:8])[CH3:4]>C(O)C>[CH2:3]([O:5][CH:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH:22]2[C:34]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:28]3[C:23]2=[CH:24][CH:25]=[CH:26][CH:27]=3)=[CH:15][CH:14]=1)[C:7]([OH:9])=[O:8])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9824017ethyl 2-ethoxy-3-[4-(2-(9H-fluoren-9-yl)ethoxy]phenyl)propionate

Product 1

HCID 98440592-Ethoxy-3-{4-[2-(9H-fluoren-9-yl)-ethoxy]-phenyl}-propionic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide (1M, 2.5 ml, 2.5 mmol) was added to a solution of ethyl 2-ethoxy-3-{4-[2-(9H-fluoren-9-yl)-ethoxy]-phenyl}-propionate (0.19 g, 0.44 mmol) in ethanol (5 ml) and the mixture stirred at room temperature for 20 h. The resulting mixture was partitioned between water (20 ml) and dichloromethane (20 ml), acidified to pH 1 by adding 1N hydrochloric acid, and the organic phase collected. The aqueous phase was further extracted with dichloromethane (3×20 ml) and the combined organics were washed with brine, dried (Na2SO4) and evaporated to give the title compound as a waxy solid; 0.17 g (95%).

Workup

  1. customThe resulting mixture was partitioned between water (20 ml) and dichloromethane (20 ml)
  2. additionby adding 1N hydrochloric acid
  3. customthe organic phase collected
  4. extractionThe aqueous phase was further extracted with dichloromethane (3×20 ml)
  5. washthe combined organics were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-0c94c8f9cd31482288cfd293efe2d8e1
Source dataset
uspto-grants-2004_01
Patent number
US06683111B2

Reaction notes

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