1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 58188252, compound

HRID 1845139Notes

Reaction equation

HRID 1845139 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][C:3]=1[S:10]([CH3:13])(=[O:12])=[O:11].C1(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:28]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:4]=1)=[N+:29]=[N-:30]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 58188263HCID 58188263, compound

Product 1

HCID 58188252HCID 58188252, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A round bottom flask was charged with (4-methyl-3-(methylsulfonyl)phenyl)methanol (6.0 g, 30.14 mmol), toluene (70 mL). Diphenyl phosphoryl azide (7.8 mL, 36.1 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (5.3 mL, 36.1 mmol) were added at 0° C. and the reaction mixture was stirred over night at room temperature. The solvent was removed under reduced pressure and the residue was diluted with water and extracted with EtOAc. The combined organic phases were concentrated under reduced pressure and the residue was purified by column chromatography to get the title compound (4 g, 62% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc
  4. concentrationThe combined organic phases were concentrated under reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-448ca9fafbea495bbb72df1e5fcfbfe5
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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