Nitromethane → (1-Nitromethyl-cyclobutyl)-acetic Acid Ethyl Ester

HRID 988735Notes

Reaction equation

HRID 988735 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH:5]=[C:6]1[CH2:9][CH2:8][CH2:7]1)[CH3:2].[N+:11]([CH3:14])([O-:13])=[O:12].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:10])[CH2:5][C:6]1([CH2:14][N+:11]([O-:13])=[O:12])[CH2:9][CH2:8][CH2:7]1)[CH3:2]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 2724141Tetrabutylammonium FluorideHCID 15724666Cyclobutylidene-acetic acid ethyl ester

Product 1

HCID 54347145(1-Nitromethyl-cyclobutyl)-acetic Acid Ethyl EsterYield 52.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The unsaturated ester (2) (5.79 g, 41.4 mmol) was dissolved in tetrahydrofuran (20 mL) and stirred at 70° C. with nitromethane (4.67 mL, 86.4 mmol) and tetrabutylammonium fluoride (1.0 M in tetrahydrofuran, 55 mL, 55.0 mmol). After 18 hours, the mixture was cooled to room temperature, diluted with ethyl acetate (150 mL), and washed with 2N HCl (60 mL) followed by brine (100 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 1:1) to give 4.34 g (52%) of a clear oil.

Workup

  1. washwashed with 2N HCl (60 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 1:1)

Sources & evidence

ORD record
ord-018f0f0cbc414716bc95ff1046ea1805
Source dataset
uspto-grants-2003_10
Patent number
US06635673B1

Reaction notes

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