Lithium Hydroxide → HCID 71254957, compound

HRID 1507629Notes

Reaction equation

HRID 1507629 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([C:13]([F:16])([F:15])[F:14])=[N:10][C:9]=2[C:17]([O:19]CC)=[O:18])=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([C:13]([F:16])([F:14])[F:15])=[N:10][C:9]=2[C:17]([OH:19])=[O:18])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 71254909HCID 71254909, compound

Product 1

HCID 71254957HCID 71254957, compoundYield 12.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound ethyl 5-(4-fluorophenyl)-2-(trifluoromethyl)oxazole-4-carboxylate (150 mg, 0.49 mmol) was dissolved in THF (4.6 mL) and cooled on ice. To this solution is added LiOH (13 mg, 0.31 mmol) in water (1.5 mL) and the mixture was stirred for 1 hr then warmed to room temperature and stirred overnight. The THF was evaporated, and H2O (10 mL) was added and the solution then acidified with 1 N HCl and extracted in EtOAc (3×15 mL). The organic fractions were dried over Na2SO4 and concentrated. The crude material was fractionated by SiO2 chromatography (DCM to 90% DCM/10% MeOH gradient, the desired product elutes in 7% MeOH) to afford a white solid (17 mg, 11% yield). 1HNMR (400 MHz, MeOD, CDCl3): d 8.17 (m, 2H), 7.14 (t, 2H, J=8 Hz).

Workup

  1. temperaturecooled on ice
  2. stirringstirred overnight
  3. customThe THF was evaporated
  4. additionH2O (10 mL) was added
  5. extractionextracted in EtOAc (3×15 mL)
  6. dry with materialThe organic fractions were dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7269cc9eba9b41fea1208389c999055a
Source dataset
uspto-grants-2015_12
Patent number
US09221805B2

Reaction notes

Loading…