Methane, dichloromethoxy- → 7-Methoxy-2-methyl-1-benzofuran-4-carbaldehyde

HRID 1091830Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091830
[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]([CH3:12])=[CH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:13][O:14]C(Cl)Cl>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:8]2[O:9][C:10]([CH3:12])=[CH:11][C:7]=2[C:6]([CH:13]=[O:14])=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 21004Methane, dichloromethoxy-HCID 112751777-Methoxy-2-methylbenzofuran

Produkt 1

HCID 110415447-Methoxy-2-methyl-1-benzofuran-4-carbaldehydeAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a well stirred solution of 7-methoxy-2-methylbenzo[b]furan (from step 2) (6.5 g, 40.07 mmol) in DCM (70.0 mL) was added stannous chloride (17.7 g, 68.26 mmol) followed by slow addition of 1,1-dichloromethyl methyl ether (4.6 g, 40.07 mmol) at −10-0° C. and stirred for 1-2 hrs. Ice cold water (100 mL) was added with vigorous stirring, the organic layer was separated and washed with water (2×50 mL) and dried over anhydrous sodium sulfate. Removal of solvent gave crude product (7.0 g). The crude product was purified by silica gel column using petroleum ether: ethyl acetate (9:1) as an eluent to afford the product as pale yellow oil (2.3 g).

Aufarbeitung

  1. customthe organic layer was separated
  2. washwashed with water (2×50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customRemoval of solvent
  5. customgave crude product (7.0 g)
  6. customThe crude product was purified by silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-008544b19a8d40e4a36f9f78d810e2b2
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129401B2

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