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

HRID 1798143ノート

反応式

HRID 1798143 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 582925842-Methoxy-6-methyl-4-phenoxy-benzaldehyde収率 63.1%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-285a7bb913c4431ba96ea82558a4629d
出典データセット
uspto-grants-2013_01
特許番号
US08343944B2

反応ノート

読み込み中…