Ethanol → 4-(4-Methoxypyrimidin-2-YL)benzaldehyde

HRID 992928노트

반응식

HRID 992928 반응식
C([O-])([O-])=O.[Na+].[Na+].C(O)C.Cl[C:11]1[N:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][N:12]=1.[CH:19]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)=[O:20]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:18][O:17][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([C:24]2[CH:25]=[CH:26][C:21]([CH:19]=[O:20])=[CH:22][CH:23]=2)[N:16]=1

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 5889352-Chloro-4-methoxypyrimidineHCID 5910734-Formylphenylboronic Acid

생성물 1

HCID 226310554-(4-Methoxypyrimidin-2-YL)benzaldehyde수율 42%

시약·촉매·용매 3

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

1 M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution of 2-chloro-4-methoxypyrimidine (2.90 g, 20.06 mmol, prepared as described in Tetrahedron 1997, 53, 11595), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.80 g (42%) of the title compound. MS 215 (M+H)+.

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe cooled reaction mixture
  4. washwashed with sat. aq. NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, 4:1 hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-9bfb078bab554320a1d46de779da1065
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06472372B1

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