Nitromethane → Methyl 3-(4,4-difluorocyclohexyl)-4-nitrobutanoate

HRID 2178505Notes

Reaction equation

HRID 2178505 reaction equation
[F:1][C:2]1([F:14])[CH2:7][CH2:6][CH:5]([CH:8]=[CH:9][C:10]([O:12][CH3:13])=[O:11])[CH2:4][CH2:3]1.[N+:15]([CH3:18])([O-:17])=[O:16].N12CCCN=C1CCCCC2>>[F:1][C:2]1([F:14])[CH2:3][CH2:4][CH:5]([CH:8]([CH2:18][N+:15]([O-:17])=[O:16])[CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123135798Methyl 3-(4,4-difluorocyclohexyl)prop-2-enoate

Product 1

HCID 89500449Methyl 3-(4,4-difluorocyclohexyl)-4-nitrobutanoateYield 68%

Procedure

Methyl 3-(4,4-difluorocyclohexyl)prop-2-enoate (4.054 g, 0.198 mol, 1 eq) is dissolved in nitromethane (23 L, 0.423 mol, 21.3 eq) and 1,8-diazabicyclo[5,4,0]undec-7-ene (3.025 g, 0.198 mol, 1 eq) is added at room temperature. The solution is stirred overnight at room temperature then evaporated. The residue is dissolved in ethyl acetate and the solution is washed with 1 M HCl and water. The organic phase is dried with MgSO4 and evaporated under vacuum. The residue is purified by chromatography over silicagel (eluent: CH2Cl2 100%) to afford methyl 3-(4,4-difluorocyclohexyl)-4-nitrobutanoate a1-20.

Workup

  1. customthen evaporated
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washthe solution is washed with 1 M HCl and water
  4. dry with materialThe organic phase is dried with MgSO4
  5. customevaporated under vacuum
  6. customThe residue is purified by chromatography over silicagel (eluent: CH2Cl2 100%)

Sources & evidence

ORD record
ord-38c60e35fb714b91b5f83ac1f29e41cf
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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