Lithium hydroxide, monohydrate → 6-(3-Chloro-phenyl)-5-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acid

HRID 632158Notes

Reaction equation

HRID 632158 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:15][CH2:14][CH2:13][O:12]2)=[C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)[N:6]=1)=[O:4].O.[OH-].[Li+]>CO.C(OCC)(=O)C>[Cl:22][C:18]1[CH:17]=[C:16]([C:7]2[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][C:8]=2[CH:11]2[CH2:15][CH2:14][CH2:13][O:12]2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 710876046-(3-Chlorophenyl)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 710875216-(3-Chloro-phenyl)-5-(tetrahydro-furan-2-yl)-pyridine-2-carboxylic acidYield 98%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 6-(3-chlorophenyl)-5-(tetrahydrofuran-2-yl)-pyridine-2-carboxylic acid methyl ester (0.3 g, 1 mmol) and lithium hydroxide monohydrate (CAN 1310-66-3, 130 mg, 3 mmol) in THF/H2O 1/1 (20 mL) was stirred at room temperature for 1 h. After removal of the organic solvent under reduced pressure the aqueous phase was washed with ethyl acetate (10 mL) and acidified with 1 N HCl to pH=3. The resulting solution was extracted with ethyl acetate (2×20 mL). The organic layer was concentrated under reduced pressure to give the title compound (0.28 g, 98%) as black oil which was used in the next step without further purification; MS (EI): m/e=304.0 [M+H]+.

Workup

  1. customAfter removal of the organic solvent under reduced pressure the aqueous phase
  2. washwas washed with ethyl acetate (10 mL)
  3. extractionThe resulting solution was extracted with ethyl acetate (2×20 mL)
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f76dc15323ff4059b8b9d28eda3c0380
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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