Water → HCID 22397119, compound

HRID 431589Notes

Reaction equation

HRID 431589 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[N:14]([CH2:20][CH:21]([OH:26])[C:22]([F:25])([F:24])[F:23])[C:13]3=[O:27])=[CH:6][CH:5]=1.I[CH3:31].O>O1CCCC1>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[N:14]([CH2:20][CH:21]([O:26][CH3:31])[C:22]([F:24])([F:25])[F:23])[C:13]3=[O:27])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22397085HCID 22397085, compound

Product 1

HCID 22397119HCID 22397119, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (45 mg, 1.0 mmol) in tetrahydrofuran (8 mL) was added 5-(4-fluoro-benzyloxy)-2-(3,3,3-trifluoro-2-hydroxy-propyl)-isoindole-1,3-dione (360 mg, 0.9 mmol) at room temperature and then iodomethane (159 mg, 1.1 mmol) was added and then after 14 h, water was added. The mixture was then extracted with ethylacetate and the combined organic extracts washed with water, brine and then dried over sodium sulfate. Filtration and evaporation gave a residue which was purified by chromatography (SiO2, hexane-EtOAc 3:1) to afford the title compound (120 mg, 32%) as a white solid. MS: m/e=398.4 (M+H+).

Workup

  1. extractionThe mixture was then extracted with ethylacetate
  2. washthe combined organic extracts washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and evaporation
  5. customgave a residue which
  6. customwas purified by chromatography (SiO2, hexane-EtOAc 3:1)

Sources & evidence

ORD record
ord-b277e086bcd54247977dd3c51cae8fa7
Source dataset
uspto-grants-2003_12
Patent number
US06660736B2

Reaction notes

Loading…