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

HRID 256199Notes

Reaction equation

HRID 256199 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:28])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[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:28])[CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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 201642021-Iodo-5-phenyl-3-pentanone

Product 1

HCID 201642191-(3',4'-Dimethoxyphenyl)-7-phenyl-2-nitro-5-heptanoneYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 36 g (0.17 mole) of 2-(3,4-dimethoxyphenyl)-1-nitroethane in 300 mL of dry tetrahydrofuran was added 71 g (0.17 mole) of 40% Triton B. The solution was stirred at room temperature for 10 min. 55.3 g (0.19 mole) of 1-iodo-5-phenyl-3-pentanone in a minimum amount of dry tetrahydrofuran was added dropwise. The mixture was stirred at room temperature for 30 min, at 50° C. for 3 hrs., 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, and concentrated at reduced pressure to give 71.5 g of crude oil. This crude material was passed through HPLC to give 46.4 g of purified material.

Workup

  1. stirringThe mixture was stirred at room temperature for 30 min, at 50° C. for 3 hrs
  2. stirringto stir at room temperature overnight
  3. customSolvent was removed in vacuo
  4. extractionextracted twice with water
  5. customThe organic layer was dried over anh
  6. concentrationMgSO4, and concentrated at reduced pressure
  7. customto give 71.5 g of crude oil

Sources & evidence

ORD record
ord-f784cffc6cdf494c9a9b1011567d0403
Source dataset
uspto-grants-1987_10
Patent number
US04701461

Reaction notes

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