Hydrochloric Acid → 1-(3,4-Dimethoxyphenyl)-7-(4-methoxyphenyl)-2-nitro-5-heptanone

HRID 66459

Reaction equation

HRID 66459 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:30])[CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.Cl.[N+](C([N+]([O-])=O)=O)([O-])=O>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:30])[CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10036050Benzene, 1,2-dimethoxy-4-(2-nitroethyl)-HCID 130650191-Iodo-5-(4-methoxyphenyl)-3-pentanoneHCID 54223030Nitro ketone

Product 1

HCID 130650201-(3,4-Dimethoxyphenyl)-7-(4-methoxyphenyl)-2-nitro-5-heptanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 15 g. (0.071 mole) of 2-(3,4-dimethoxyphenyl)-1-nitroethane in 200 ml. of dry tetrahydrofuran was added 33.45 g. (0.08 mole) of 40% Triton B at room temperature. The solution was stirred at room temperature for 14 minutes under N2. 22.6 g. (0.071 mole) of 1-iodo-5-(4-methoxyphenyl)-3-pentanone was then added in portions. The mixture was heated at 50°-55° for 2 hours under N2 until no more starting material was detected on TLC, and then cooled to room temperature. The resulting reaction solution was poured into cold dil. HCl and extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4. The crude material was chromatographed on Florisil to provide 22 g. of desired nitro ketone derivative. Recrystallization from 80% ethanol gave a white solid which has m.p. 87°-89° C.

Workup

  1. customat room temperature
  2. temperatureThe mixture was heated at 50°-55° for 2 hours under N2 until
  3. temperaturecooled to room temperature
  4. customThe resulting reaction solution
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. customThe crude material was chromatographed on Florisil
  8. customto provide 22 g
  9. customRecrystallization from 80% ethanol
  10. customgave a white solid which

Sources & evidence

ORD record
ord-3f5f0db0de82463591055f422ac4d9a0
Source dataset
uspto-grants-1982_08
Patent number
US04342692

Linked notes

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