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

HRID 256199Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 256199
[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]

Komponenten

4

Edukt 2

HCID 10036050Benzene, 1,2-dimethoxy-4-(2-nitroethyl)-HCID 201642021-Iodo-5-phenyl-3-pentanone

Produkt 1

HCID 201642191-(3',4'-Dimethoxyphenyl)-7-phenyl-2-nitro-5-heptanoneAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f784cffc6cdf494c9a9b1011567d0403
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04701461

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