4-Nitrobenzaldehyde → 1-(4-Nitrophenyl)2-nitro-heptan-1-ol

HRID 2107367

Reaktionsgleichung

Reaktionsgleichung von HRID 2107367
[Li]CCCC.[N+:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([O-:8])=[O:7].[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1)([O-:17])=[O:16].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>C1COCC1.C(Cl)Cl>[N+:15]([C:18]1[CH:19]=[CH:20][C:21]([CH:22]([OH:23])[CH:9]([N+:6]([O-:8])=[O:7])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:24][CH:25]=1)([O-:17])=[O:16]

Komponenten

7

Edukt 4

HCID 5414-NitrobenzaldehydeHCID 6049Ethylenediaminetetraacetic AcidHCID 125891-NitrohexaneHCID 178418339Butyllithium

Produkt 1

HCID 148173291-(4-Nitrophenyl)2-nitro-heptan-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

n-BuLi (1.6 M in hexane, 6.24 mL) was added dropwise with stirring to a solution of nitrohexane (1.4 mL, 10 mmol) in THF (12 mL) at -78° C. After 15 minutes a solution of TiCl3 (OPriso) (5 mmol) in THF (2 mL) and CH2Cl2 (3 mL) solution was added. After a further 15 minutes 4-nitrobenzaldehyde (0.75 mL, 5 mmol) in CH2Cl2 (3 mL) was added and the mixture allowed to warm up to room temperature (18 30 min.). Stirring was continued for a further 3.5 hours at room temperature and the mixture was quenched with an aqueous slurry of disodium EDTA (1.86 g, 5 mmol) and extracted with Et2O (3×75 mL), aqueous sodium bicarbonate (75 mL) and water (75 mL), dried and evaporated in vacuo. Flash column chromatography [SiO2, hexane:Et2O, 4:1 v/v] gave 1-(4-nitrophenyl)2 -nitro-heptan-1-ol (1.13 g, 81% Erythro:threo ratio 3.9:1

Aufarbeitung

  1. extractionextracted with Et2O (3×75 mL), aqueous sodium bicarbonate (75 mL) and water (75 mL)
  2. customdried
  3. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7821a067a32a48798f43deb21c16d3d1
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04933505

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