Pyridine → 2-Methoxy-6-methyl-4-phenoxy-benzaldehyde

HRID 1798143Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798143
[OH:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.C(Cl)Cl.[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1C=CC=CC=1>CC#N.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([O:1][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:9]=[C:8]([CH3:10])[C:5]=1[CH:6]=[O:7]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 66827Phenylboronic AcidHCID 143093964-Hydroxy-2-methoxy-6-methylbenzaldehyde

Produkt 1

HCID 582925842-Methoxy-6-methyl-4-phenoxy-benzaldehydeAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 4-hydroxy-2-methoxy-6-methyl-benzaldehyde (1.00 g, 6.02 mmol), powdered 4A molecular sieves (4 g) in CH3CN (40 mL) and DCM (40 mL) was treated with phenylboronic acid (1.47 g, 12.06 mmol), followed by copper (II) acetate (1.09 g, 6.00 mmol). Pyridine (2.40 mL, 29.70 mmol) was added to the green suspension and the resulting mixture was stirred at rt overnight in an open flask. The mixture was filtered through a pad of Celite and the filtrate was concentrated to a green oil. The residue was purified by column chromatography (SiO2, EtOAc/hexanes; 1:9) to afford 2-methoxy-6-methyl-4-phenoxy-benzaldehyde (0.92 g, 63%), as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.52 (s, 1H), 7.41 (t, J=7.42 Hz, 2H), 7.22 (t, J=7.42 Hz, 1H), 7.08 (d, J=7.42 Hz, 2H), 6.43 (d, J=2.34 Hz, 1H), 6.31 (d, J=2.34 Hz, 1H), 3.83 (s, 3H), 2.53 (s, 3H).

Aufarbeitung

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated to a green oil
  3. customThe residue was purified by column chromatography (SiO2, EtOAc/hexanes; 1:9)

Quellen und Nachweise

ORD-Eintrag
ord-285a7bb913c4431ba96ea82558a4629d
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

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