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

HRID 1798143노트

반응식

HRID 1798143 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 582925842-Methoxy-6-methyl-4-phenoxy-benzaldehyde수율 63.1%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-285a7bb913c4431ba96ea82558a4629d
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343944B2

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