Isopropanol → Benzene, 1,2-dimethoxy-4-(2-nitroethyl)-

HRID 65295

Reaktionsgleichung

Reaktionsgleichung von HRID 65295
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][N+:8]([O-:10])=[O:9].CC(O)C.[BH4-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][CH2:7][N+:8]([O-:10])=[O:9])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Komponenten

5

Edukt 3

HCID 3776IsopropanolHCID 2220933,4-Dimethoxy-beta-nitrostyreneHCID 4311764Sodium borohydride

Produkt 1

HCID 10036050Benzene, 1,2-dimethoxy-4-(2-nitroethyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The nitrostyrene derivative (3) is then cooled to about -10°-10° C., treated with silica gel, and reduced using 1.5-4 equivalents of a boron-based reducing agent, e.g., sodium borohydride, with 2-propanol and an inert solvent, e.g., CH2Cl2, at -10°-10° C. for 20-60 minutes to produce a nitrophenylethane derivative of formula 4 (step 2). For example, 3,4-dimethoxy-β-nitrostyrene (3) is treated with 2-propanol and SiO2 in CH2Cl2 at 0°-10° C. for 20 minutes, followed by reduction with 1.5 eq NaBH4 at 5° C. for 30 minutes to yield 2-(3,4-dimethoxyphenyl)nitroethane (4).

Quellen und Nachweise

ORD-Eintrag
ord-bd801b358ea64efea972f6bb1885035d
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04613606

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