Hydrochloric Acid → 6-(3,5-Difluoro-4-hydroxybenzyl)-8-[5-fluoro-2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]oct-7-enoic acid

HRID 1921902Notes

Reaction equation

HRID 1921902 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[C:44]([F:47])[C:45]=1[OH:46])[CH2:5][CH:6]([CH:16]=[CH:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13]CC)=[O:12].[OH-].[Na+].Cl>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:43]=[C:44]([F:47])[C:45]=1[OH:46])[CH2:5][CH:6]([CH:16]=[CH:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:34]=[CH:35][C:36]([C:39]([F:41])([F:42])[F:40])=[CH:37][CH:38]=2)=[CH:29][CH:28]=1)[CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 76678032Ethyl 6-(3,5-difluoro-4-hydroxybenzyl)-8-[5-fluoro-2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)-phenyl]oct-7-enoate

Product 1

HCID 866365116-(3,5-Difluoro-4-hydroxybenzyl)-8-[5-fluoro-2-(4'-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]oct-7-enoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

400 mg (0.61 mmol) of ethyl 6-(3,5-difluoro-4-hydroxybenzyl)-8-[5-fluoro-2-(4′-trifluoromethylbiphenyl-4-ylmethoxy)phenyl]oct-7-enoate are stirred overnight at 50° C. with 73 mg (1.83 mmol) of sodium hydroxide in a mixture of 20 ml of THF and 10 ml of water. The cooled mixture is acidified with dilute hydrochloric acid and extracted with ethyl acetate, and the combined organic phases are dried over sodium sulfate and concentrated. 333 mg (86% of theory) of the title compound are obtained as E/Z mixture (2:1).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined organic phases are dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d02fdcb40a924264b7e822a49d8ffcf3
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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