Hydrochloric Acid → HCID 10096338, compound

HRID 1391808Notes

Reaction equation

HRID 1391808 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([C:14]2[CH:15]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[O:30][CH2:31][C:32]([O:34]CC)=[O:33].O.[OH-].[Na+].Cl>C1COCC1>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]([C:14]2[CH:15]=[C:16]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:28])[F:29])=[CH:22][CH:21]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:10][CH2:11][CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[O:30][CH2:31][C:32]([OH:34])=[O:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58629947HCID 58629947, compound

Product 1

HCID 10096338HCID 10096338, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl {[2-methyl-4-({1-[4′-(trifluoromethyl)-3-biphenylyl]pentyl}oxy)phenyl]oxy}acetate (138 mg, 0.28 mmol) was dissolved in THF (1.5 mL), water (0.5 mL) and aqueous NaOH (2M, 0.52 mL, 1.04 mmol) and the mixture stirred at 70° C. for 2 hours, cooled to rt and acidified to pH4 with aqueous hydrochloric acid (2M). The mixture was then partitioned between EtOAc and water, the layers separated and the organic layer washed with brine, dried (Na2SO4) and concentrated to give the title compound as a colourless gum (130 mg).

Workup

  1. customThe mixture was then partitioned between EtOAc and water
  2. customthe layers separated
  3. washthe organic layer washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2334459f58604b42ac173dc9389b841f
Source dataset
uspto-grants-2008_03
Patent number
US07338960B2

Reaction notes

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