1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59226521, compound

HRID 2192559Notes

Reaction equation

HRID 2192559 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][C:9]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])=[CH:8][CH2:7]1)(=O)=O.C1CCN2C(=NCCC2)CC1>O1CCCC1.C(OCC)(=O)C>[C:9]1([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])[CH2:10][CH2:11][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59226499HCID 59226499, compound

Product 1

HCID 59226521HCID 59226521, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(3-nitropyridin-4-yl)cyclohex-3-enyl methanesulfonate (1.0 equiv) in tetrahydrofuran (0.1 M) was added DBU (1.8 equiv.) at room temperature. The reaction mixture was stirred at rt overnight. The reaction mixture was diluted with ethyl acetate (200 mL), and washed with sat NaCl (30 mL). The organic was dried with MgSO4, filtered and concentrated. The residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes) to give 4-(cyclohexa-1,3-dienyl)-3-nitropyridine. LC/MS (m/z): MH+=203.2, Rt=0.85.

Workup

  1. washwashed
  2. dry with materialThe organic was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-24f13be205504977a37a77ce06ba5137
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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