Sodium Hydroxide → {2-Methyl-4-[(z)-3-phenyl-3-(4-pyridin-2-ylethynyl-phenyl)-allyloxy]-phenoxy}-acetic acid

HRID 549911Notes

Reaction equation

HRID 549911 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13]/[CH:14]=[C:15](/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)\[C:16]2[CH:21]=[CH:20][C:19]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:18][CH:17]=2)=[CH:8][C:7]=1[CH3:36].[OH-].[Na+]>CO>[CH3:36][C:7]1[CH:8]=[C:9]([O:12][CH2:13]/[CH:14]=[C:15](/[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)\[C:16]2[CH:21]=[CH:20][C:19]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[CH:18][CH:17]=2)[CH:10]=[CH:11][C:6]=1[O:5][CH2:4][C:3]([OH:37])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67146898HCID 67146898, compound

Product 1

HCID 23634358{2-Methyl-4-[(z)-3-phenyl-3-(4-pyridin-2-ylethynyl-phenyl)-allyloxy]-phenoxy}-acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the above ester (239 mg, 0.488 mmol) in methanol (40 ml) was added 1N NaOH (0.975 ml, 0.975 mmol) and the mixture were refluxed for 2 hr. After cooling to room temperature the mixture were evaporated in vacuo. The residue was dissolved in dichloromethane (50 mL) and extracted with water (10 ml). The aqueous phase was acidified with 1N HCl (1 ml) pH 3 and extracted with dichloromethane (20 ml). The dichloromethane phase were dried with anhydrous magnesium sulfate and subsequently evaporated in vacuo yielding the title acid as light green foam.

Workup

  1. temperaturethe mixture were refluxed for 2 hr
  2. customwere evaporated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  4. extractionextracted with water (10 ml)
  5. extractionextracted with dichloromethane (20 ml)
  6. dry with materialThe dichloromethane phase were dried with anhydrous magnesium sulfate
  7. customsubsequently evaporated in vacuo
  8. customyielding the title acid as light green foam

Sources & evidence

ORD record
ord-118261a2a88945faa7e638d0cb9b9cee
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

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