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

HRID 992928ノート

反応式

HRID 992928 の反応式
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

参加物

8

反応物 4

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

生成物 1

HCID 226310554-(4-Methoxypyrimidin-2-YL)benzaldehyde収率 42%

試薬・触媒・溶媒 3

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-9bfb078bab554320a1d46de779da1065
出典データセット
uspto-grants-2002_10
特許番号
US06472372B1

反応ノート

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