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

HRID 66472Notes

Reaction equation

HRID 66472 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]([Cl: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]([Cl: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 201641905-Iodo-1-(4'-chlorophenyl)-3-pentanone

Product 1

HCID 201641881-(3',4'-Dimethoxyphenyl)-7-(4'-chlorophenyl)-2-nitro-5-heptanoneYield 69.6%

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 g (0.23 mole) of 40% Triton B. The solution was stirred at room temperature for 10 min. 70.3 g (0.23 mole) of 5-iodo-1-(4'-chlorophenyl)-3-pentanone in a minimum amount of dry tetrahydrofuran was added dropwise. The mixture was heated at 50° C. for 3 hr., 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. The crude concentrate was passed through HPLC to give 65 g of purified material.

Workup

  1. temperatureThe mixture was heated at 50° C. for 3 hr
  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. concentrationThe crude concentrate

Sources & evidence

ORD record
ord-3b694296a737479eb3b7ee11c73c2fd4
Source dataset
uspto-grants-1982_08
Patent number
US04342692

Reaction notes

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