Hydrochloric Acid → 5-Cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinic acid

HRID 469773

Reaction equation

HRID 469773 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:7]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[N:6][CH:5]=1.C1COCC1.O.[OH-].[Li+].Cl>O>[CH:10]1([C:8]2[C:7]([O:16][CH2:17][C:18]([F:21])([F:19])[F:20])=[N:6][CH:5]=[C:4]([CH:9]=2)[C:3]([OH:22])=[O:2])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 71294015Methyl 5-cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinate

Product 1

HCID 712939525-Cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinic acidYield 101.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Cyclohexyl-6-(2,2,2-trifluoroethoxy)nicotinic acid methyl ester (95 mg, 299 μmol) was combined with THF (4 mL) and water (2 mL) to give a light yellow solution. Lithium hydroxide hydrate (25.1 mg, 599 μmol) was added under argon. The reaction mixture was stirred at ambient temperature over night; poured into 6 mL 2 M HCl solution and extracted with i-propyl acetate (2×60 mL). The organic layers were combined, dried over Na2SO4 and concentrated in vacuo to give the title compound (92 mg, quant.) as white solid that was used in the subsequent reactions without further purification; MS (ESI) 302.0 (M−H)−.

Workup

  1. customto give a light yellow solution
  2. extractionextracted with i-propyl acetate (2×60 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e39dfebc7aa94f58bc09824be7b733a8
Source dataset
uspto-grants-2014_01
Patent number
US08629166B2

Linked notes

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