Sodium Carbonate → Methyl-2-formyl-7-methoxybenzo[b]furan-4-carboxylate

HRID 548971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 548971
[CH3:1][O:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]([CH2:14]Br)[O:10][C:9]=2[C:8]([O:16][CH3:17])=[CH:7][CH:6]=1)=[O:4].C(=O)([O-])[O-:19].[Na+].[Na+]>CS(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[C:13]2[CH:12]=[C:11]([CH:14]=[O:19])[O:10][C:9]=2[C:8]([O:16][CH3:17])=[CH:7][CH:6]=1)=[O:4]

Komponenten

5

Edukt 2

HCID 10340Sodium CarbonateHCID 66592982Methyl-2-bromomethyl-7-methoxybenzo[b]furan-4-carboxylate

Produkt 1

HCID 86636828Methyl-2-formyl-7-methoxybenzo[b]furan-4-carboxylateAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a well stirred solution of Methyl-2-bromomethyl-7-methoxybenzo[b]furan-4-carboxylate (step 6) (3.1 g, 10.36 mmol) in dimethyl sulfoxide (30.0 mL) was added powdered sodium carbonate (1.64 g, 15.55 mmol) at 90-95° C. and stirred for 2-3 hours. Reaction mixture was cooled to room temperature and diluted with water (300 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with water (2×50 mL) and dried over anhydrous sodium sulfate. Removal of solvent gave crude product (2.9 g) as brown viscous oil. Purification by silica gel column using chloroform: ethyl acetate (95:5) as an eluent afforded 2.2 g of pure product.

Aufarbeitung

  1. customReaction mixture
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic layers were washed with water (2×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of solvent
  6. customgave crude product (2.9 g) as brown viscous oil
  7. customPurification by silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-8e834821abed4fe5ad094ba58cf0fed4
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943634B2

Notizen zur Reaktion

Wird geladen…