Nitromethane → HCID 58718575, compound

HRID 1244826Notes

Reaction equation

HRID 1244826 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH:5]=[C:6]1[CH2:10][C@H:9]([CH3:11])[C@H:8]([CH3:12])[CH2:7]1)[CH3:2].[N+:14]([CH3:17])([O-:16])=[O:15].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1([CH2:17][N+:14]([O-:16])=[O:15])[CH2:7][C@@H:8]([CH3:12])[C@H:9]([CH3:11])[CH2:10]1)[CH3:2]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 2724141Tetrabutylammonium FluorideHCID 54234077HCID 54234077, compound

Product 1

HCID 58718575HCID 58718575, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The unsaturated ester (2) (1.384 g, 7.60 mmol) was dissolved in tetrahydrofuran (10 mL) and stirred at 70° C. with nitromethane (0.82 mL, 15.2 mmol) and tetrabutylammonium fluoride (1.0M in tetrahydrofuran, 11.4 mL, 11.4 mmol). After 6 hours, the mixture was cooled to room temperature, diluted with ethyl acetate (50 mL) and washed with 2N HCl (30 mL) followed by brine (50 mL). The organic phase was collected, dried (MgSO4), and the solvent removed in vacuo. The residue was purified by flash chromatography (silica, ethyl acetate:heptane 5:95) to give 0.837 g (45%) of a clear oil.

Workup

  1. washwashed with 2N HCl (30 mL)
  2. customThe organic phase was collected
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by flash chromatography (silica, ethyl acetate:heptane 5:95)

Sources & evidence

ORD record
ord-d52838ce094d42fe8d0ccf2f72c67972
Source dataset
uspto-grants-2006_10
Patent number
US07122678B2

Reaction notes

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