Sodium Iodide → 2-Nitro-6-(2-oxoethyl)benzoic Acid Methyl Ester

HRID 133109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 133109
[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:5]=1[CH:13]=[CH:14][O:15]C.[Na+].[I-].C[Si](Cl)(C)C>CC#N>[CH3:1][O:2][C:3](=[O:17])[C:4]1[C:5]([CH2:13][CH:14]=[O:15])=[CH:6][CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 674228532-(2-Methoxyvinyl)-6-nitrobenzoic Acid Methyl Ester

Produkt 1

HCID 866906922-Nitro-6-(2-oxoethyl)benzoic Acid Methyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-methoxy-vinyl)-6-nitro-benzoic acid methyl ester (Step A, 3.33 g, 14.1 mmol, 1.0 eq) and CH3CN (20 mL) was added NaI (2.3 g, 15.5 mmol, 1.1 eq) and TMSCl (2 mL, 15.5 mmol, 1.1 eq). The reaction was stirred at RT for 4 h, then quenched with saturated NH4Cl and extracted with EtOAc. The organic layer was washed with H2O and brine, dried (MgSO4) and concentrated in vacuo to give a red-orange oil. Purification by silica flash chromatography (0-30% EtOAc:hexane) gave the desired compound as an orange oil.

Aufarbeitung

  1. customquenched with saturated NH4Cl
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto give a red-orange oil
  7. customPurification by silica flash chromatography (0-30% EtOAc:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-dcb414ecfee04c93870763d0454e2051
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390820B2

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