Lithium hydroxide, monohydrate → HCID 64159628, compound

HRID 2224658Notes

Reaction equation

HRID 2224658 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[N:8][O:9][C:10]=1[CH:11]([CH3:13])[CH3:12])=[O:5])C.O[Li].O>C1COCC1.O>[CH:11]([C:10]1[O:9][N:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[C:6]=1[C:4]([OH:5])=[O:3])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 69107640HCID 69107640, compound

Product 1

HCID 64159628HCID 64159628, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 15 g crude 5-isopropyl-3-(3-fluoro-phenyl)-isoxazole-4-carboxylic acid ethyl ester and 10.08 g (240 mmol) LiOH.H2O in 75 mL THF, 50 mL water was heated under reflux for 15 h. The mixture was concentrated, acidified and extracted with ethyl acetate. The combined organic extracts were dried with Na2SO4 and evaporated to yield 4.1 g (33% in two steps) of the title compound as a light yellow solid. (m/e): 250.1 (MH+; 100%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 h
  3. concentrationThe mixture was concentrated
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-bfad1b8ce18b479d8ce2f5dd899ae7b5
Source dataset
uspto-grants-2008_05
Patent number
US07378435B2

Reaction notes

Loading…