Trimethylsilyldiazomethane → Methyl 2-amino-4,6-dimethoxybenzoate

HRID 871392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871392
[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([OH:6])=[O:5].[CH3:15][Si](C=[N+]=[N-])(C)C>CO.C1COCC1.C(OCC)C>[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([O:6][CH3:15])=[O:5]

Komponenten

6

Edukt 2

HCID 167693TrimethylsilyldiazomethaneHCID 116584562-Amino-4,6-dimethoxybenzoic acid

Produkt 1

HCID 11550253Methyl 2-amino-4,6-dimethoxybenzoateAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 2-amino-4,6-dimethoxybenzoic acid (7.888 g, 40 mmol) in MeOH (40 mL) and THF (40 mL) at room temperature was dropped 2.0 M solution of (trimethylsilyl)diazomethane in diethyl ether. The mixture was stirred at room temperature overnight. After the solvent was evaporated under reduced pressure, water and EtOAc was added to the residue. The organic layer was separated, dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by silica gel chromatography with 20-40% EtOAc/hexane as eluants to afford methyl 2-amino-4,6-dimethoxybenzoate as a solid (6.462 g, 76%). 1H NMR (300 MHz, CDCl3) δ 5.83 (d, 1H), 5.78 (d, 1H), 5.53 (br, 2H), 3.86 (s, 3H), 3.80 (s, 3H), 3.77 (s, 3H); LC-MS (ESI) m/z 212 (M+H)+.

Aufarbeitung

  1. customAfter the solvent was evaporated under reduced pressure, water and EtOAc
  2. additionwas added to the residue
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography with 20-40% EtOAc/hexane as eluants

Quellen und Nachweise

ORD-Eintrag
ord-db9d0c1db7724b09ab51498698d30c21
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969587B2

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