Tetrahydrofuran → 3-Fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoic acid

HRID 1669324Notes

Reaction equation

HRID 1669324 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:37])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:13]([C:20]2[CH:21]=[N:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[C:8]([F:36])[CH:7]=1.O1CCCC1>CO>[F:36][C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][C:9]=1[O:12][CH:13]([C:20]1[CH:21]=[N:22][C:23]([C:26]2[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=2)=[CH:24][CH:25]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:5]([OH:37])=[O:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 673420373-Fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoic acid methyl ester

Product 1

HCID 673440023-Fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoic acidYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium hydroxide (5.0N, 0.09 mL, 0.42 mmol) to 3-fluoro-4-{1-[6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-heptyloxy}-benzoic acid methyl ester (0.04 g, 0.085 mmol) in methanol (2 mL). Add tetrahydro-furan (1 ml) and stir for four hours. Acidify with 1.0 N HCl and extract desired compound with ethyl acetate three times. Dry organic fractions with Na2SO4, filter and concentrate under reduced pressure to provide 0.035 g (90%) of title compound.

Workup

  1. extractionAcidify with 1.0 N HCl and extract desired compound with ethyl acetate three times
  2. filtrationDry organic fractions with Na2SO4, filter
  3. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-a225cd20af964f75a2faa6d2365e4a57
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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