Nitromethane → HCID 86603441, compound

HRID 1028651Notes

Reaction equation

HRID 1028651 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]([O:17][CH2:18]C)=[O:16])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[N+:22]([CH3:25])([O-:24])=[O:23].[OH-].[CH2:27]([N+](CCCC)(CCCC)CCCC)CCC>[Cl-].[NH4+]>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([CH:13]([CH:25]([N+:22]([O-:24])=[O:23])[CH3:27])[CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH:4]=[C:3]([C:2]([F:1])([F:21])[F:20])[CH:8]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 2723671Tetrabutylammonium HydroxideHCID 57370822HCID 57370822, compound

Product 1

HCID 86603441HCID 86603441, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

Ethyl 3-[3,5-bis(trifluoromethyl)phenyl]acrylate (170 mg, 0.54 mmol) and nitromethane (736 uL, 10.29 mmol) were treated with a solution of tetrabutylammonium hydroxide (1.0 M solution in MeOH, 1.5 mL) and the mixture heated to reflux for 3 h, diluted with 10% aqueous ammonium chloride (10 mL) and extracted with EtOAC (4×30 mL). The combined organic extracts were washed with 10% ammonium chloride (20 mL), dried over MgSO4, concentrated in vacuo to give the crude product. This was purified by flash chromatography using 10% EtOAC/hexanes to afford methyl 3-[3,5-bis(trifluoro methyl)phenyl]-4-nitropentanoate as a colorless oil. 1H NMR (CDCl3, 500 MHz) δ 7.82 (br s 1H), 7.64 (br s, 2H), 4.91 (m, 1H), 3.91 (m, 1H), 3.61 (s, 3H), 2.82 (m, 2H), 1.42 (d, J=6.7 Hz, 3H).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 3 h
  3. extractionextracted with EtOAC (4×30 mL)
  4. washThe combined organic extracts were washed with 10% ammonium chloride (20 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give the crude product
  8. customThis was purified by flash chromatography

Sources & evidence

ORD record
ord-5a8999a4f0e14b1da082784743e9cbc2
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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