Lithium hydroxide, monohydrate → HCID 68881844, compound

HRID 2111013Notes

Reaction equation

HRID 2111013 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14]([C:15]([O:17]C)=[O:16])=[CH:13][O:12][N:11]=2)=[CH:6][CH:5]=1.O.[OH-].[Li+]>C1COCC1.O>[Cl:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:14]([C:15]([OH:17])=[O:16])=[CH:13][O:12][N:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68881871HCID 68881871, compound

Product 1

HCID 68881844HCID 68881844, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Methyl 3-(4-(2-chloroethyl)phenyl)isoxazole-4-carboxylate (1.46 g, 5.49 mmol) was dissolved in THF-water (2:1, 30 ml), lithium hydroxide monohydrate (922 mg, 21.97 mmol) was added, and the mixture was stirred at room temperature for 6 hours. THF was evaporated under reduced pressure, 2N hydrochloric acid was added to weak-acidify the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (1.38 g, 100%).

Workup

  1. customTHF was evaporated under reduced pressure, 2N hydrochloric acid
  2. additionwas added to weak-acidify the reaction mixture
  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. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f8d13d536dd640d2b11aca057b07845f
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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