Nitric Acid → HCID 101043616, Verbindung

HRID 925121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 925121
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:19]#[N:20])[CH2:18][CH2:17][CH2:16]2)=[CH:11][C:10]=1[O:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.[N+:30]([O-])([OH:32])=[O:31]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([O:21][CH3:22])=[CH:11][C:12]([C:15]2([C:19]#[N:20])[CH2:18][CH2:17][CH2:16]2)=[C:13]([N+:30]([O-:32])=[O:31])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 921355081-(4-(Benzyloxy)-3-methoxyphenyl)-cyclobutanecarbonitrile

Produkt 1

HCID 101043616HCID 101043616, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1-(4-(benzyloxy)-3-methoxyphenyl)cyclobutanecarbonitrile (5 g, 17.04 mmol), from Step 1, in acetic acid (20 mL)/acetic anhydride (20 mL) was cooled in an ice bath to 0° C. and treated slowly with 65% nitric acid (2.54 mL, 34.1 mmol). The reaction was stirred at 0° C. for 20 min, poured into ice and extracted with EtOAc. Organic layer was washed with saturated aqueous NaHCO3 and water. Organic layer was dried (MgSO4), filtered and concentrated. Purification by flash chromatography (silica gel, 5-50% EtOAc/hexane) afforded 1-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrile (5.29 g, 92%). MS (ESI) m/z 339 (M+H)+.

Aufarbeitung

  1. additionpoured into ice
  2. extractionextracted with EtOAc
  3. washOrganic layer was washed with saturated aqueous NaHCO3 and water
  4. dry with materialOrganic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (silica gel, 5-50% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-386300b954d34cb0b5618c78ffab2b9d
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284272B2

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