Nitromethane → HCID 18335047, compound

HRID 2296780Notes

Reaction equation

HRID 2296780 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]=1)=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[N+:29]([CH3:32])([O-:31])=[O:30]>O1CCCC1.C(OCC)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[CH2:32][N+:29]([O-:31])=[O:30])=[O:4]

Participants

6

Reactant 3

HCID 6375NitromethaneHCID 87647Methyl cyclohex-1-ene-1-carboxylateHCID 2724141Tetrabutylammonium Fluoride

Product 1

HCID 18335047HCID 18335047, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of cyclohex-1-enecarboxylic acid methyl ester 1 (5.15 g; 36.7 mmol), tetrabutyl ammonium fluoride (55.10 mL; 1 M in THF; 55.1 mmol) and nitromethane (3.97 mL; 73.5 mmol) in tetrahydrofuran (60 mL) was heated to reflux for 4 hours. After cooling to room temperature, the reaction mixture was diluted with diethyl ether (500 mL), washed with 2N HCl (2×100 mL) and then with brine (2×100 mL). The phases were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The crude mixture was purified over silica gel chromatography (EtOAc/heptane 1:4) to give 2 (5.46 g; cis and trans isomers; 73%) as a pale yellow liquid.

Workup

  1. temperatureto reflux for 4 hours
  2. washwashed with 2N HCl (2×100 mL)
  3. customThe phases were separated
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was purified over silica gel chromatography (EtOAc/heptane 1:4)
  7. customto give 2 (5.46 g; cis and trans isomers; 73%) as a pale yellow liquid

Sources & evidence

ORD record
ord-b8851fd6005c4fd7b9be37250ddbbaf4
Source dataset
uspto-grants-2002_12
Patent number
US06489352B2

Reaction notes

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