Hydrochloric Acid → HCID 12674909, compound

HRID 1779988Notes

Reaction equation

HRID 1779988 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[N+:8]([CH2:11][CH2:12][CH3:13])([O-:10])=[O:9].Cl>C(#N)C.O>[CH3:4][CH:3]([CH:11]([N+:8]([O-:10])=[O:9])[CH2:12][CH3:13])[CH2:2][C:1]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 79031-NitropropaneHCID 638132Methyl Crotonate

Product 1

HCID 12674909HCID 12674909, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 4 g (40 mmol) of methyl crotonate and 4.72 g (53 mmol) of 1-nitropropane in 20 mL of acetonitrile was treated with 6 mL (40 mmol) of 1,8-diazobicyclo[5.4.0]undec-7-ene (DBU). After stirring for 22 h at room temperature the reaction mixture was diluted with water and acidified with 2N HCl. The solution was extracted with Et2O and the Et2O layer was washed with brine, dried and concentrated. The residue was chromagraphed on a flash column using 10% Et2O-Hexane to isolate 6.41 g (85%) of the title compound.

Workup

  1. extractionThe solution was extracted with Et2O
  2. washthe Et2O layer was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-792a5b228d6f4814a5f607fdfb0b8d3c
Source dataset
uspto-grants-1997_05
Patent number
US05629322

Reaction notes

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