Water → HCID 22930021, compound

HRID 1296005Notes

Reaction equation

HRID 1296005 reaction equation
[CH2:1]([C:3]1[N:8]=[CH:7][C:6]([CH2:9]O)=[CH:5][CH:4]=1)[CH3:2].C1(P([N:25]=[N+:26]=[N-:27])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:25]=[N+:26]=[N-:27])=[CH:5][CH:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 22929790(6-Ethylpyridin-3-yl)methanol

Product 1

HCID 22930021HCID 22930021, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving (6-ethyl-3-pyridyl)methanol (2.25 g, 16.4 mmol) in toluene (25 ml), diphenylphosphoryl azide (4.2 ml, 19.6 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.9 ml, 19.6 mmol) were added while stirring on ice, and the mixture was further stirred at room temperature for 18 hours. Water was added for treatment and extraction was performed with ethyl acetate. The extract was washed with brine and then dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (2.2 g) as a yellow oil. (84.5% yield)

Workup

  1. additionwere added
  2. stirringthe mixture was further stirred at room temperature for 18 hours
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-6bcd0e354ba34994a837ebd5e87e3c84
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

Loading…