Sodium hydride → HCID 121386214, compound

HRID 2202951Notes

Reaction equation

HRID 2202951 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:10][OH:11])[CH:7]=[CH:8][CH:9]=1.Cl[C:13]1[CH:18]=[CH:17][N+:16]([O-:19])=[CH:15][CH:14]=1>C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH2:10][O:11][C:13]1[CH:18]=[CH:17][N+:16]([O-:19])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 701173-Chlorobenzyl alcoholHCID 707244-chloropyridine N-oxide

Product 1

HCID 121386214HCID 121386214, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold suspension of NaH (40% oil dispersion, 1.51 g) in THF (60 ml) was added (3-chlorophenyl)methanol (3.0 g) at 0° C. The reaction mixture was stirred at the same temperature for 30 min followed by the portionwise addition of 4-chloropyridine 1-oxide (2.73 g) at 0° C. The resulting reaction mixture was stirred for 1 h at 0° C. and then warmed to room temperature. After 2 h, the reaction mixture was poured into ice-water (100 g) and extracted with DCM. The DCM layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was triturated with Et2O to give the title compound (2.2 g) as a brown solid.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 1 h at 0° C.
  3. waitAfter 2 h
  4. extractionextracted with DCM
  5. washThe DCM layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-3f6dfe77fca345eaab4eb87689d3d22a
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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