Lithium Hydroxide → HCID 67121085, compound

HRID 1510451Notes

Reaction equation

HRID 1510451 reaction equation
C([O:4][CH2:5][C:6]1[C:10]([Cl:11])=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[C:14]([F:22])[CH:13]=2)[O:8][N:7]=1)(=O)C.[Li+].[OH-]>O1CCCC1>[Cl:11][C:10]1[C:6]([CH2:5][OH:4])=[N:7][O:8][C:9]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[C:14]([F:22])[CH:13]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67121146HCID 67121146, compound

Product 1

HCID 67121085HCID 67121085, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (4-chloro-5-(3-fluoro-4-(trifluoromethyl)phenyl)isoxazol-3-yl)methyl acetate (1 g, 2.96 mmol) in tetrahydrofuran (20 mL) an aqueous solution of 1N LiOH (8.88 mL, 8.88 mmol) was added. The biphasic reaction mixture was stirred vigorously for 3 hours at 60° C., then allowed to cool and left to stand over the weekend. The reaction mixture was transferred to a separating funnel and the organic layer removed. The aqueous layer was extracted with diethyl ether (2×20 mL), the organics were combined, washed with water (20 mL) and brine (20 mL) before drying with Na2SO4. Filtration and evaporation to dryness in vacuo afforded (4-chloro-5-(3-fluoro-4-(trifluoromethyl)phenyl)isoxazol-3-yl)methanol (878 mg, 2.97 mmol).

Workup

  1. customThe biphasic reaction mixture
  2. temperatureto cool
  3. waitleft
  4. customThe reaction mixture was transferred to a separating funnel
  5. customthe organic layer removed
  6. extractionThe aqueous layer was extracted with diethyl ether (2×20 mL)
  7. washwashed with water (20 mL) and brine (20 mL)
  8. dry with materialbefore drying with Na2SO4
  9. filtrationFiltration and evaporation to dryness in vacuo

Sources & evidence

ORD record
ord-f8024d8f06e94eba89178ec7051aceef
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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