Sodium hydride → HCID 89559051, compound

HRID 510491Notes

Reaction equation

HRID 510491 reaction equation
[H-].[Na+].[O:3]1[CH2:6][CH:5]([OH:7])[CH2:4]1.F[C:9]1[CH:10]=[CH:11][C:12]([N+:16]([O-:18])=[O:17])=[C:13]([CH3:15])[CH:14]=1>C1COCC1.O>[CH3:15][C:13]1[CH:14]=[C:9]([CH:10]=[CH:11][C:12]=1[N+:16]([O-:18])=[O:17])[O:7][CH:5]1[CH2:6][O:3][CH2:4]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 949565-Fluoro-2-nitrotolueneHCID 9942117Oxetan-3-ol

Product 1

HCID 89559051HCID 89559051, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.084 g, 2.11 mmol) was added to a solution of oxetan-3-ol (0.12 g, 1.62 mmol) in THF (10 mL) at 0° C. The mixture was stirred at 0° C. for 20 minutes, after which time a solution of 5-fluoro-2-nitrotoluene (0.26 g, 1.62 mmol) in THF (10 mL) was added. The mixture was allowed to warm to room temperature, and stirring was continued for 16 h. The reaction mixture was diluted with water and extracted with DCM. The organic layer was washed with brine. The organic layer was concentrated under vacuum and the resulting crude material was purified by column chromatography (silica gel: 100-200 mesh, 8-30% EtOAc/hexane) to give the title compound (0.18 g, 54%) as a yellow gum. LCMS (ES+) no mass ion observed, RT 1.71 minutes (method 2).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirring
  3. waitwas continued for 16 h
  4. extractionextracted with DCM
  5. washThe organic layer was washed with brine
  6. concentrationThe organic layer was concentrated under vacuum
  7. customthe resulting crude material was purified by column chromatography (silica gel: 100-200 mesh, 8-30% EtOAc/hexane)

Sources & evidence

ORD record
ord-4d47b5215877433fac2a6a72b77e75ff
Source dataset
uspto-grants-2015_08
Patent number
US09096614B2

Reaction notes

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