1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54065281, compound

HRID 980484Notes

Reaction equation

HRID 980484 reaction equation
Br[CH:2]([C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1)[CH2:3][CH:4]([O:10][C:11](=[O:13])[CH3:12])[CH2:5][O:6][C:7](=[O:9])[CH3:8].N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[C:11]([O:10][CH:4]([CH2:5][O:6][C:7](=[O:9])[CH3:8])[CH:3]=[CH:2][C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 20221555HCID 20221555, compound

Product 1

HCID 54065281HCID 54065281, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

7.0 g of 2-(1-bromo-3,4-diacetoxybutyl)pyrazine (4102 and 4103) was dissolved in 100 ml of toluene, 3.3 g of 1,8-diazabicyclo [5.4.0]undec-7-ene added under an argon atmosphere and the solution heated overnight at 65°-70°. It was then cooled, the toluene solution decanted and concentrated in vacuo. The residue was chromatographed on silica gel (hexane/ethyl acetate) to yield 3.5 g of 2-(3,4-diacetoxy-1-butenyl)pyrazine (4104) as a pale yellow oil. UV EtOH max: 240 (4.14), 292 (3.85), 298 (3.86).

Workup

  1. temperaturethe solution heated overnight at 65°-70°
  2. temperatureIt was then cooled
  3. customthe toluene solution decanted
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c72f0ca1e95949bb8cc118be73755b54
Source dataset
uspto-grants-1987_01
Patent number
US04638005

Reaction notes

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