Nitric Acid → HCID 178500687, Verbindung

HRID 1713795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1713795
[N+:1]([O-:4])(O)=[O:2].S(=O)(=O)(O)O.[C:10]1([C@H:16]2[CH2:21][CH2:20][C@H:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:18][CH2:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)(Cl)Cl>[N+:1]([C:13]1[CH:14]=[CH:15][C:10]([C@H:16]2[CH2:17][CH2:18][C@H:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:20][CH2:21]2)=[CH:11][CH:12]=1)([O-:4])=[O:2]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 178500650HCID 178500650, Verbindung

Produkt 1

HCID 178500687HCID 178500687, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 65% nitric acid (3.95 mL) and 95% sulphuric acid (4.97 mL) was added dropwise to a stirred solution of methyl (trans-4-phenylcyclohexyl)acetate (4710 mg) in CCl4 (20 mL) at 5° C. and the solution was allowed to warm to ambient temperature and stirred for 16 hours. Ice/water (50 mL) was added and the mixture was extracted with DCM (2×40 mL). The organic extracts were combined, washed with brine (50 mL), dried, and concentrated in vacuo to give an oil. This oil was purified by flash chromatography on a 80 g Biotage™ silica column, using a gradient of 0-20% EtOAc in hexane as the eluent to give crude methyl [trans-4-(4-nitrophenyl)cyclohexyl]acetate which was dissolved in ethyl acetate (30 mL). 10% palladium on carbon (0.400 g) was added and the resulting suspension was stirred at ambient temperature for 16 hours under an atmosphere of hydrogen. The suspension was filtered through diatomaceous earth and concentrated in vacuo to give a solid. This was purified by flash chromatography on a 40 g Biotage™ silica column using a gradient of 20-45% EtOAc/hexane as eluent to give the title compound (1740 mg) as a solid; 1H NMR δ 6.83 (2H, d), 6.46 (2H, d), 4.72 (2H, s), 3.59 (3H, s), 2.23 (3H, m), 1.72 (5H, m), 1.35 (2H, m), 1.09 (2H, m); MS m/e MH+ 248.

Aufarbeitung

  1. extractionthe mixture was extracted with DCM (2×40 mL)
  2. washwashed with brine (50 mL)
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customThis oil was purified by flash chromatography on a 80 g Biotage™ silica column

Quellen und Nachweise

ORD-Eintrag
ord-712757450d6f43eaa38796fef10fb0c2
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795283B2

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