Water → HCID 86612606, compound

HRID 1436094Notes

Reaction equation

HRID 1436094 reaction equation
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH:25](O)[CH3:26])=[N:23][CH:24]=1.N12CCCN=C1CCCCC2.O>C1(C)C=CC=CC=1.C(OCC)C>[N:15]([CH:25]([C:22]1[CH:21]=[CH:20][C:19]([Cl:18])=[CH:24][N:23]=1)[CH3:26])=[N+:16]=[N-:17]

Participants

7

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 690032511-(5-chloropyridin-2-yl)ethanol

Product 1

HCID 86612606HCID 86612606, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

Diphenylphosphoryl azide (1.0 mL) was added to a solution of 1-(5-chloropyridin-2-yl)ethanol (503 mg) in toluene (8 mL) in a nitrogen atmosphere. The reaction solution was ice-cooled, and 1,8-diazabicyclo[5,4,0]undec-7-ene (0.69 mL) was added dropwise to the solution. The reaction solution was stirred for three hours. Then, the solution was returned to room temperature and stirred overnight. Water and diethyl ether were added to the reaction solution, and the organic layer was separated. The organic layer was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane-diethyl ether) to obtain 337 mg of the title compound.

Workup

  1. temperaturecooled
  2. customwas returned to room temperature
  3. stirringstirred overnight
  4. customthe organic layer was separated
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (elution solvent: hexane-diethyl ether)

Sources & evidence

ORD record
ord-5922c45044cc4decbc223128349d93d5
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

Loading…