Benzene, 1,2-dimethoxy-4-(2-nitroethyl)- → 1-(3',4'-Dimethoxyphenyl)-7-(4'-fluorophenyl)-2-nitro-5-heptanone

HRID 66469Notes

Reaction equation

HRID 66469 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N+:13]([O-:15])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].I[CH2:17][CH2:18][C:19](=[O:29])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([N+:13]([O-:15])=[O:14])[CH2:17][CH2:18][C:19](=[O:29])[CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 10036050Benzene, 1,2-dimethoxy-4-(2-nitroethyl)-HCID 201641911-Iodo-5-(4'-fluorophenyl)-3-pentanone

Product 1

HCID 201642101-(3',4'-Dimethoxyphenyl)-7-(4'-fluorophenyl)-2-nitro-5-heptanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 48.5 g (0.23 mole) of 2-(3',4'-dimethoxyphenyl)-1-nitroethane in 400 ml of dry tetrahydrofuran was added 96.0 (0.23 mole) of 40% Triton B. The solution was stirred at room temperature for 10 minutes. 66.7 g (0.23 mole) of 1-iodo-5-(4'-fluorophenyl)-3-pentanone in a minimum amount of dry tetrahydrofuran was added dropwise. The mixture was heated at 50° C. for 3 hours, then allowed to stir at room temperature overnight. Solvent was removed in vacuo and the residue taken up in ether and extracted twice with water. The organic layer was dried over anh MgSO4, filtered and concentrated at reduced pressure to obtain a crude oil. The crude material was passed through HPLC to give 79 g purified material.

Workup

  1. temperatureThe mixture was heated at 50° C. for 3 hours
  2. stirringto stir at room temperature overnight
  3. customSolvent was removed in vacuo
  4. extractionextracted twice with water
  5. dry with materialThe organic layer was dried over anh MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated at reduced pressure
  8. customto obtain a crude oil
  9. customto give 79 g
  10. custompurified material

Sources & evidence

ORD record
ord-6a1d297513064215b385e581ad57e718
Source dataset
uspto-grants-1982_08
Patent number
US04342692

Reaction notes

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