2-Nitropropane → HCID 77230587, compound

HRID 1392707Notes

Reaction equation

HRID 1392707 reaction equation
[N+]([CH:4]([CH3:6])[CH3:5])([O-])=O.C([O-])([O-])=O.[K+].[K+].[Br:13][C:14]1[CH:19]=[CH:18][C:17](/[CH:20]=[C:21](\[C:29]#[N:30])/[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:16][CH:15]=1>CCO.CCOC(C)=O>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]2[C:21]([C:29]#[N:30])([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[C:4]2([CH3:6])[CH3:5])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 3982-NitropropaneHCID 11430Potassium CarbonateHCID 86598120HCID 86598120, compound

Product 1

HCID 77230587HCID 77230587, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Following a procedure described in Tetrahedron Lett. 1985, 1923, a mixture of 2-nitropropane (1 eq), K2CO3 (1 eq) and ester from step 1 (1 eq) in EtOH (1.2M) was stirred at 100° C. in a close bottle for 3 h. The mixture was cooled to rt, diluted with EtOAc, washed with a NH4Cl sol., brine, dried over MgSO4, filtered and concentrated. Flash chromatography (hexane:EtOAc, 95:5) afforded the title compound as oil.

Workup

  1. temperatureThe mixture was cooled to rt
  2. washwashed with a NH4Cl sol., brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0a7f3b1b64044d06bd5fee3b42f56b46
Source dataset
uspto-grants-2008_03
Patent number
US07342024B2

Reaction notes

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