Sodium borohydride → 1-(3,4-Dimethoxyphenyl)-2-nitro-6-cyano-6-(prop-2-yl)-6-(3,4-dimethoxyphenyl)hexane

HRID 65300

Reaktionsgleichung

Reaktionsgleichung von HRID 65300
C(O[CH:5]([CH2:21][CH2:22][C:23]([C:37]#[N:38])([CH:34]([CH3:36])[CH3:35])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=1)[CH:6]([N+:18]([O-:20])=[O:19])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)(=O)C.[BH4-].[Na+]>CC(O)C>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([CH2:7][CH:6]([N+:18]([O-:20])=[O:19])[CH2:5][CH2:21][CH2:22][C:23]([C:37]#[N:38])([CH:34]([CH3:36])[CH3:35])[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=2)[CH:13]=[CH:12][C:11]=1[O:14][CH3:15]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 13745755O-acetyl-1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexan-3-ol

Produkt 1

HCID 137457561-(3,4-Dimethoxyphenyl)-2-nitro-6-cyano-6-(prop-2-yl)-6-(3,4-dimethoxyphenyl)hexane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

The resulting nitrohexanol acetate of formula 9 is then reduced using a boron-based reducing agent, e.g., sodium borohydride, in a 2° or 3° alkanol at 25°-80° C. for 3-15 hours to produce a nitrohexane derivative of formula 10 (step 8). For example, O-acetyl-1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexan-3-ol (9) is heated with NaBH4 in 2-propanol at reflux for 3-15 hours to yield 1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(prop-2-yl)-6-(3,4-dimethoxyphenyl)hexane (10).

Aufarbeitung

  1. temperatureat reflux for 3-15 hours

Quellen und Nachweise

ORD-Eintrag
ord-44d5231dab924a04a07eb18702dcc546
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04613606

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