Lithium hydroxide, monohydrate → 4-(5-(Trifluoromethyl)isoxazol-3-yl)benzoic acid

HRID 572263Notes

Reaction equation

HRID 572263 reaction equation
C([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)=[CH:7][CH:6]=1)C.O.[OH-].[Li+]>C1COCC1>[F:19][C:16]([F:17])([F:18])[C:14]1[O:13][N:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:20])=[O:3])=[CH:6][CH:7]=2)[CH:15]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 576061044-(5-Trifluoromethyl-isoxazol-3-yl)-benzoic acid ethyl ester

Product 1

HCID 576061124-(5-(Trifluoromethyl)isoxazol-3-yl)benzoic acidYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(5-Trifluoromethyl-isoxazol-3-yl)-benzoic acid ethyl ester (Preparative Example 9, 2.25 g, 7.86 mmol) in THF (20 mL) was treated with an aqueous solution (5 mL) of lithium hydroxide monohydrate (660 mg, 15.72 mmol) and allowed to stir for 16 hr. The reaction was then evaporated to a small volume and treated with a 1 N aqueous hydrochloric acid solution (25 mL) and the resulting solids filtered, washed with water and air dried to afford product as a colorless solid (1.48 g, 73%). 1H NMR (DMSO-d6) 8.06 (s, 4H), 8.13 (s, 1H). 13C NMR 106.5, 118.0 (q, J=270), 127.9, 130.8, 131.2, 132.4, ˜150 quartet not resolved from baseline noise, 133.8, 162.8, 167.3. 19F NMR −63.6. LC/MS 6.04 min, [M+1]+ 258.

Workup

  1. customThe reaction was then evaporated to a small volume
  2. additiontreated with a 1 N aqueous hydrochloric acid solution (25 mL)
  3. filtrationthe resulting solids filtered
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-c3f192f9df8d495f9d2153c629d90def
Source dataset
uspto-grants-2015_05
Patent number
US09029397B2

Reaction notes

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