Lithium hydroxide, monohydrate → HCID 71087846, compound

HRID 927510Notes

Reaction equation

HRID 927510 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:15][CH2:14][O:13][CH2:12]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][O:13][CH2:12]2)[CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 71087516HCID 71087516, compound

Product 1

HCID 71087846HCID 71087846, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of 6-(3-chlorophenyl)-5-(tetrahydrofuran-3-yl)-pyridine-2-carboxylic acid methyl ester (0.15 g, 0.5 mmol) and lithium hydroxide monohydrate (CAN 1310-66-3, 88 mg, 2.1 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 combined organic layer was concentrated under reduced pressure to provide the title compound (0.12 g, 81%) as black oil which was used in the next step without further purification; MS (EI): m/e=304.1 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-9e5a780ffece43b2a6e6a6c47d7dd003
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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