1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 69073571, compound

HRID 730171Notes

Reaction equation

HRID 730171 reaction equation
[Br-].[Br:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[C:5]([C:29]([O:31][CH3:32])=[O:30])[CH:4]=1.C1CCN2C(=NCCC2)CC1.[CH3:44][O:45][C:46]1[C:47]([CH3:54])=[C:48]([CH:51]=[CH:52][CH:53]=1)[CH:49]=O>C(#N)C>[CH3:32][O:31][C:29](=[O:30])[C:5]1[CH:4]=[C:3]([Br:2])[CH:28]=[CH:27][C:6]=1[CH:7]=[CH:49][C:48]1[CH:51]=[CH:52][CH:53]=[C:46]([O:45][CH3:44])[C:47]=1[CH3:54]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 131626633-Methoxy-2-methylbenzaldehydeHCID 86614762HCID 86614762, compound

Product 1

HCID 69073571HCID 69073571, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of (4-bromo-2-methoxycarbonylbenzyl)-triphenylphosphonium bromide (4) (34.2 g; 60.0 mmol), DBU (1,8-diazabicyclo(5.4.0) undec-5-ene; 20.1 g; 132 mmol), and 3-methoxy-2-methylbenzaldehyde (7.21 g; 48.0 mmol) in acetonitrile were heated at reflux temperature for 2 hours. The mixture was cooled and the solvent was evaporated. The residue was partitioned between water and ethyl acetate and the organic phase was washed with 0.1 N HCl, water, and brine. The solution was dried over MgSO4, filtered, and evaporated. The residue was crystallized from ethyl acetate and hexane to yield compound 5 (14.5 g; 84%).

Workup

  1. temperaturewere heated
  2. temperatureat reflux temperature for 2 hours
  3. temperatureThe mixture was cooled
  4. customthe solvent was evaporated
  5. customThe residue was partitioned between water and ethyl acetate
  6. washthe organic phase was washed with 0.1 N HCl, water, and brine
  7. dry with materialThe solution was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-0e555f41981a4dc9be380bdcd1338a99
Source dataset
uspto-grants-2009_09
Patent number
US07582667B2

Reaction notes

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