Lithium Hydroxide → HCID 86727014, compound

HRID 1770636Notes

Reaction equation

HRID 1770636 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][C:12]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[C:20]([N+:28]([O-:30])=[O:29])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[Li+]>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][C:12]([C:18]3[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[C:20]([N+:28]([O-:30])=[O:29])[CH:19]=3)([C:14]([F:15])([F:17])[F:16])[O:11][N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86727015HCID 86727015, compound

Product 1

HCID 86727014HCID 86727014, compoundYield 388.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-[3-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-5-yl]-2-nitrobenzoate (1 g, 0.43 mmol) and lithium hydroxide (73 mg) in tetrahydrofuran (20 ml) and water (10 ml) was stirred for 1 hour at room temperature. Tetrahydrofuran was then removed and the residue was extracted with ethyl acetate (2×25 ml). The combined organic layers were dried over sodium sulfate and concentrated to give 4-[3-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-5-yl]-2-nitrobenzoic acid (0.75 g), 1H-NMR (400 MHz, DMSO): 7.85-7.87 (2H, m), 7.82 (1H, m), 7.66-7.69 (1H, m), 7.61-7.62 (2H, m), 4.22-4.46 (2H, m) ppm.

Workup

  1. customTetrahydrofuran was then removed
  2. extractionthe residue was extracted with ethyl acetate (2×25 ml)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-aaa561b30c7240bf97b869911317cb9b
Source dataset
uspto-grants-2016_02
Patent number
US09247740B2

Reaction notes

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