Nitromethane → HCID 54405957, compound

HRID 1859088Notes

Reaction equation

HRID 1859088 reaction equation
C1CCN2C(=NCCC2)CC1.[CH2:12]([O:14][C:15](=[O:22])[CH:16]=[CH:17][CH2:18][CH:19]1[CH2:21][CH2:20]1)[CH3:13].[N+:23]([CH3:26])([O-:25])=[O:24]>CC#N>[CH2:12]([O:14][C:15](=[O:22])[CH2:16][CH:17]([CH2:26][N+:23]([O-:25])=[O:24])[CH2:18][CH:19]1[CH2:20][CH2:21]1)[CH3:13]

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53920553HCID 53920553, compound

Product 1

HCID 54405957HCID 54405957, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

DBU (4.1 g, 26.9 mmol) is added to a solution of 4-cyclopropyl-2-butenoic acid ethyl ester (3.4 g, 26.9 mmol) and nitromethane (9.13 g, 135 mmol) in 20 mL of CH3CN. The solution is warmed to 60° C. under Ar for 4 hours, then stirred at room temperature overnight. The CH3CN is evaporated, and the residue is taken up in 50 mL of EtOAc. The solution is washed with saturated KH2PO4 (3×50 mL) followed by 50 mL of brine. The organic layer is dried over Na2SO4 and evaporated to give an oil which is chromatographed (MPLC) over silica gel with 25% EtOAc/hexane to give 2.4 g of 4-cyclopropyl-3-nitromethyl-butanoic acid ethyl ester 3.

Workup

  1. customThe CH3CN is evaporated
  2. washThe solution is washed with saturated KH2PO4 (3×50 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. customevaporated
  5. customto give an oil which
  6. customis chromatographed (MPLC) over silica gel with 25% EtOAc/hexane

Sources & evidence

ORD record
ord-08c033a80eb84aaa924ce6c875019b7a
Source dataset
uspto-grants-2000_11
Patent number
US06153650

Reaction notes

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