Toluene → Ethyl 2-(4-methoxybenzoyl)-4-nitromethyl-3-(1,3-benzodioxole-5-yl)butyrate

HRID 1272525

Reaktionsgleichung

Reaktionsgleichung von HRID 1272525
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8])=[CH:5][CH:4]=1.[N+:17]([CH:20]=[CH:21][C:22]1[CH:30]=[CH:29][C:25]2OCOC=2C=1)([O-:19])=[O:18].[C:31]([O:34][CH2:35][CH3:36])(=[O:33])C.[C:37]1(C)C=CC=CC=1>C(Cl)Cl.N12CCCN=C1CCCCC2>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([CH:9]([CH:22]([C:30]2[CH:29]=[CH:25][C:36]3[O:33][CH2:31][O:34][C:35]=3[CH:37]=2)[CH2:21][CH2:20][N+:17]([O-:19])=[O:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:8])=[CH:15][CH:16]=1

Komponenten

7

Edukt 4

HCID 1140Toluene2×HCID 8857Ethyl AcetateHCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl esterHCID 949455-(2-Nitroethenyl)-1,3-benzodioxole

Produkt 1

HCID 22322609Ethyl 2-(4-methoxybenzoyl)-4-nitromethyl-3-(1,3-benzodioxole-5-yl)butyrate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneKatalysator2×HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To ethyl (4-methoxybenzoyl)acetate (23.0 g, 0.104 mol), prepared by the method of Krapcho et al., Org. Syn. 47, 20 (1967), and 5-(2-nitrovinyl)-1,3-benzodioxole (17.0 g, 0.088 mol) dissolved in 180 mL of toluene and heated to 80° C. was added 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU, 0.65 g) with stirring. The mixture was heated until all the nitro starting material dissolved. The solution was stirred without heating for 30 minutes (min) and then an additional 0.65 g of DBU was added. After stirring an additional 45 minutes, thin layer chromatography (5% ethyl acetate in methylene chloride) indicated the absence of nitro starting material. Toluene (200 mL) was added, and the organic phase was washed with dilute hydrochloric acid and NaCl solution. The organic phase was dried over sodium sulfate and then concentrated under reduced pressure. The residue obtained was chromatographed on silica gel eluting with 3:1 hexane-ethyl acetate to give 21.22 g of the desired product as a mixture of isomers and 9.98 g. of recovered ethyl (4-methoxybenzoyl)acetate.

Aufarbeitung

  1. dissolutiondissolved
  2. stirringThe solution was stirred
  3. temperaturewithout heating for 30 minutes (min)
  4. stirringAfter stirring an additional 45 minutes
  5. washthe organic phase was washed with dilute hydrochloric acid and NaCl solution
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. customwas chromatographed on silica gel eluting with 3:1 hexane-ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-b099aa45c7334e929395ed01ea8e6013
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208517B1

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