Lithium hydroxide, monohydrate → HCID 86668163, compound

HRID 385064Notes

Reaction equation

HRID 385064 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:15]#[CH:16])[C:12]=1[O:13][CH3:14])[C:6]([O:8]C)=[O:7])#[N:2].O.[OH-].[Li+]>O1CCCC1.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([C:15]#[CH:16])[C:12]=1[O:13][CH3:14])[C:6]([OH:8])=[O:7])#[N:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86668160HCID 86668160, compound

Product 1

HCID 86668163HCID 86668163, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-cyano-5-ethynyl-4-methoxybenzoate (640 mg) was dissolved in tetrahydrofuran (6 mL) and water (3 mL), and lithium hydroxide monohydrate (495 mg) was added to the solution, and then the mixture was stirred at room temperature for 3 hours. The solvent was distilled off under reduced pressure and 1N hydrochloric acid was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (610 mg) as a brown crystal.

Workup

  1. distillationThe solvent was distilled off under reduced pressure and 1N hydrochloric acid
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5e0fcd9399074506bc70cf6371faa4fe
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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