Water → HCID 22929711, compound

HRID 1295990Notes

Reaction equation

HRID 1295990 reaction equation
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.[CH2:29]([O:31][C:32]1[C:33]([CH3:41])=[C:34]([CH2:39]O)[CH:35]=[N:36][C:37]=1[CH3:38])[CH3:30].O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:29]([O:31][C:32]1[C:33]([CH3:41])=[C:34]([CH2:39][N:15]=[N+:16]=[N-:17])[CH:35]=[N:36][C:37]=1[CH3:38])[CH3:30]

Participants

7

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 22930062HCID 22930062, compound

Product 1

HCID 22929711HCID 22929711, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diphenylphosphoryl azide (0.59 ml, 2.7 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.41 ml, 2.7 mmol) were added dropwise in that order to a solution of (5-ethoxy-4,6-dimethyl-3-pyridyl)methanol (0.415 g, 2.29 mmol) in toluene (5 ml) at room temperature, and the mixture was stirred for 16 hours. After confirming completion of the reaction by thin layer chromatography, the mixture was poured into water and extraction was performed with ethyl acetate. The extract was washed with saturated aqueous NaCl and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (447 mg, 95%) as a colorless oil.

Workup

  1. customcompletion of the reaction by thin layer chromatography
  2. washThe extract was washed with saturated aqueous NaCl
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-a118b23c6ce3464bb7af0cf16a53138f
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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