1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86711834, compound

HRID 623746Notes

Reaction equation

HRID 623746 reaction equation
[N+:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[C-:2].C1CCN2C(=NCCC2)CC1.[F:20][C:21]1[CH:26]=[CH:25][C:24](/[CH:27]=[C:28](/[N+]([O-])=O)\[CH3:29])=[CH:23][CH:22]=1>C1COCC1>[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:28]([CH3:29])=[CH:2][NH:1][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 533707Ethyl isocyanoacetateHCID 5371949775-31-5

Product 1

HCID 86711834HCID 86711834, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl isocyanoacetate (4.36 mL, 42.09 mmol) and DBU (6.28 mL, 42.09 mmol) was added to a solution of (E)-1-fluoro-4-(2-nitroprop-1-enyl)benzene (6.0 g, 33.14 mmol) in THF (60 mL) at 0° C. The reaction mixture was stirred for 30 min at room temperature; quenched with water (100 mL) and extracted with EtOAc (2×100 mL). The combined organic layers were washed with water (1×100 mL) and brine (75 mL), dried (Na2SO4) and concentrated under reduced pressure to give the crude product, which was purified by column chromatography (silica gel; 60-120 mesh). The pure product was eluted with 10% EtOAc in petroleum ether to yield the desired compound (6.0 g, 73%) as pale yellow solid.

Workup

  1. customquenched with water (100 mL)
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic layers were washed with water (1×100 mL) and brine (75 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product, which
  7. customwas purified by column chromatography (silica gel; 60-120 mesh)
  8. washThe pure product was eluted with 10% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-71d7a15bb40e4ce089c892899822b786
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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