Lithium hydroxide, monohydrate → HCID 25210999, compound

HRID 572268Notes

Reaction equation

HRID 572268 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([C:11]2[C:15]([CH3:16])=[C:14]([CH:17]([F:19])[F:18])[O:13][N:12]=2)=[CH:9][CH:10]=1)=[O:5])C.O.[OH-].[Li+]>C1COCC1>[F:19][CH:17]([F:18])[C:14]1[O:13][N:12]=[C:11]([C:8]2[S:7][C:6]([C:4]([OH:5])=[O:3])=[CH:10][CH:9]=2)[C:15]=1[CH3:16]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 25211000HCID 25211000, compound

Product 1

HCID 25210999HCID 25210999, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(5-Difluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carboxylic acid ethyl ester (Preparative Example 25, 1.0 g, 3.48 mmol) in THF (20 mL) was treated with an aqueous solution (5 mL) of lithium hydroxide monohydrate (292 mg, 6.96 mmol) and allowed to stir for 20 hr. The reaction was then evaporated to a small volume and treated with a 1 N aqueous hydrochloric acid solution to a pH of ˜2 and the resulting solids filtered, washed with water and air dried to afford product as a colorless solid (900 mg, 99%). 1H NMR (DMSO-d6) 2.29 (s, 3H), 7.44 (t, J=51.9, 1H), 7.66 (d, J=2.6, 1H), 7.78 (d, J=2.6, 1H). 13C NMR 7.7, 108.1 (t, J=236), 115.0, 130.3, 134.3, 134.5, 137.4, 157.8, 159.6 (t, J=26), 163.1. 19F NMR −118.8 (J=51.5). LC/MS 5.41 min, [M+1]+ 260.

Workup

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

Sources & evidence

ORD record
ord-060cde461129411995bfe4083aadde5b
Source dataset
uspto-grants-2015_05
Patent number
US09029397B2

Reaction notes

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