Dimethyl 5-(1-hydroxy-2-nitroethyl)isophthalate → Dimethyl 5-(2-nitrovinyl)isophthalate

HRID 587937Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587937
O[CH:2]([C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])[CH2:3][N+:4]([O-:6])=[O:5]>C(Cl)Cl.C(OC(=O)C)(=O)C.CN(C)C1C=CN=CC=1>[N+:4]([CH:3]=[CH:2][C:7]1[CH:8]=[C:9]([C:17]([O:19][CH3:20])=[O:18])[CH:10]=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])([O-:6])=[O:5]

Komponenten

5

Edukt 1

HCID 68474723Dimethyl 5-(1-hydroxy-2-nitroethyl)isophthalate

Produkt 1

HCID 68478188Dimethyl 5-(2-nitrovinyl)isophthalate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
22 °C

Versuchsvorschrift

To a solution of 2.29 g (8.09 mmol) of dimethyl 5-(1-hydroxy-2-nitroethyl)isophthalate in 50 mL of DCM and 10 mL of acetic anhydride at 22° C. was added 100 mg of 4-dimethylaminopyridine. The solution was stirred at 22° C. for 1.5 h, evaporated and then coevaporated with xylenes (the material darkened slightly). The residue was partitioned between 100 mL of DCM and 50 mL of 1 N HCl. The organic layer was washed with water (50 mL), satd NaHCO3, dried (Na2SO4) and evaporated. The resulting residue was purified by flash chromatography on silica gel eluting with DCM to give dimethyl 5-(2-nitrovinyl)isophthalate as a light yellow solid.

Aufarbeitung

  1. customevaporated
  2. customThe residue was partitioned between 100 mL of DCM and 50 mL of 1 N HCl
  3. washThe organic layer was washed with water (50 mL), satd NaHCO3
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe resulting residue was purified by flash chromatography on silica gel eluting with DCM

Quellen und Nachweise

ORD-Eintrag
ord-779c57fb7faa4cbc952e9c7e62459a33
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227918B2

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