Sodium Hydroxide → HCID 67344003, compound

HRID 1669258Notes

Reaction equation

HRID 1669258 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:14]=[CH:13][C:12]([CH:15]([O:18][C:19]3[CH:29]=[CH:28][C:22]([C:23]([O:25]CC)=[O:24])=[CH:21][CH:20]=3)[CH2:16][CH3:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>C(O)C>[F:30][C:2]([F:1])([F:31])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:14]=[CH:13][C:12]([CH:15]([O:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:28][CH:29]=3)[CH2:16][CH3:17])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67342661HCID 67342661, compound

Product 1

HCID 67344003HCID 67344003, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-propoxy-1-ol (280 mg, 1.0 mmol) in THF (2 mL) and toluene (4 mL) is added 1,1′-(azodicarbonyl)dipiperidine (ADDP, 376.8 mg, 1.49 mmol) at 0° C., followed by the addition of triphenylphosphine (391.6 mg, 1.49 mmol) and methyl 4-hydroxybenzoate (181.7 mg, 1.19 mmol). The reaction mixture is warmed up to room temperature and stirred overnight. The mixture is loaded on silica gel, eluted with hexanes with a gradient from 0% of ethyl acetate to 50% of ethyl acetate giving ethyl 4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-propoxy}-benzoate (350 mg). The ester product is taken into ethanol (4 mL), treated with sodium hydroxide (5N aqueous, 1 mL) for 3 h at 40° C. The mixture is concentrated, diluted with ethyl acetate, acidified with 5 N HCl (1.1 mL), extracted with ethyl acetate. The organic layers are dried and concentrated giving 4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-propoxy}-benzoic acid (345 mg).

Workup

  1. concentrationThe mixture is concentrated
  2. additiondiluted with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. customThe organic layers are dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d60ccdcfbd6e4555acd09346fc97bf48
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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