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

HRID 1523429Notes

Reaction equation

HRID 1523429 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 (0.1M) 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-c67e63f10a7245f190767e10da34e88d
Source dataset
uspto-grants-2015_07
Patent number
US09079889B2

Reaction notes

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