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

HRID 1249516Notes

Reaction equation

HRID 1249516 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 113.2%

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 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, 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 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. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-d3ce5c7d2d0e44058bbca942bbb85aff
Source dataset
uspto-grants-1986_12
Patent number
US04632929

Reaction notes

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