1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 118023486, compound

HRID 1497008Notes

Reaction equation

HRID 1497008 reaction equation
[CH2:1](O)/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]CC.C1(P([N:28]=[N+:29]=[N-:30])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[N:28]([CH2:1]/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[N+:29]=[N-:30]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 64364912,4-Dodecadien-1-ol, (2E,4E)-

Product 1

HCID 118023486HCID 118023486, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2E,4E)-Dodeca-2,4-dien-1-ol (4.95 g) was dissolved in dry toluene (110 ml) and diphenylphosphinyl azide (7.92 g) was added. DBU (4.91 ml) was added dropwise. The mixture turned opaque under evolution of heat. The solvent was evaporated and diethyl ether was added to the residue. The reaction mixture was washed with 1M HCl, 1M NaOH and brine and the organic layer was dried over sodium sulfate, filtered and concentrated to give a light yellow liquid. The crude product was filtered over silica gel.

Workup

  1. temperatureof heat
  2. customThe solvent was evaporated
  3. additiondiethyl ether was added to the residue
  4. washThe reaction mixture was washed with 1M HCl, 1M NaOH and brine
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a light yellow liquid
  9. filtrationThe crude product was filtered over silica gel

Sources & evidence

ORD record
ord-b0107944063d4cbeb3bd51ff3aa6bcb9
Source dataset
uspto-grants-2015_12
Patent number
US09199948B2

Reaction notes

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