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

HRID 65304

Reaktionsgleichung

Reaktionsgleichung von HRID 65304
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+].Cl.O>C(O)(C)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

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 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 reaction mixture containing 1-(3,4-dimethoxyphenyl)-2-nitro-3-acetoxy-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexane (9) prepared in Preparation 7(A) was cooled to room temperature and diluted with isopropanol (350 mL). Solid NaBH4 (15 g, 0.4 mol) was added over 15 minutes at 25° C. The mixture was then heated to reflux (about 40° C.) for 15 hours, then cooled to 5° C. A solution of 10% HCl (30 mL) was slowly added, followed by water (100 mL). The organic layer was extracted, washed with saturated aqueous NH4Cl (200 mL), and saturated aqueous NaHCO3 (200 mL). The organic layer was evaporated to yield 1-(3,4-dimethoxyphenyl)-2-nitro-6-cyano-6-(i-propyl)-6-(3,4-dimethoxyphenyl)hexane (10, 58.7 g, m.p. 107°-110° C., MS m/e 470(M+)) as a pale yellow solid.

Aufarbeitung

  1. temperatureThe mixture was then heated
  2. temperatureto reflux (about 40° C.) for 15 hours
  3. temperaturecooled to 5° C
  4. extractionThe organic layer was extracted
  5. washwashed with saturated aqueous NH4Cl (200 mL), and saturated aqueous NaHCO3 (200 mL)
  6. customThe organic layer was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-4ef6e8fd000c478b95e59c60bc068954
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04613606

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