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

HRID 927544Notes

Reaction equation

HRID 927544 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-abe2a51ce52c41ffa5131a00a8f34ea6
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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