Hydrochloric Acid → 5-Cyclohex-1-enyl-6-(2,2,2-trifluoroethoxy)nicotinic acid

HRID 469769Notes

Reaction equation

HRID 469769 reaction equation
C[O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([C:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH: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>[C: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])[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 712944455-Cyclohex-1-enyl-6-(2,2,2-trifluoroethoxy)nicotinic acid methylester

Product 1

HCID 712941075-Cyclohex-1-enyl-6-(2,2,2-trifluoroethoxy)nicotinic acidYield 104.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Cyclohex-1-enyl-6-(2,2,2-trifluoroethoxy)nicotinic acid methylester (0.03 g, 95.2 μmol) was combined with THF (0.3 mL) and water (0.15 mL) to give a light yellow solution. Lithium hydroxide hydrate (7.99 mg, 190 μmol) was added under argon. The reaction mixture was stirred at room temperature overnight, poured into 2 mL 2 M HCl and extracted with i-propyl acetate (2×20 mL). The organic layers were combined, dried with Na2SO4 and concentrated in vacuo to give the title compound (30 mg, quant) as white solid that was used in the subsequent reactions without further purification; MS (ESI) 300.2 (M−H)−.

Workup

  1. customto give a light yellow solution
  2. extractionextracted with i-propyl acetate (2×20 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-421bd99c9c364a8bbd16347ae90f9b98
Source dataset
uspto-grants-2014_01
Patent number
US08629166B2

Reaction notes

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