Sodium Carbonate → (E)-3-[4-(3-Pyridinyl)phenyl]-2-propenal

HRID 2416458ノート

反応式

HRID 2416458 の反応式
C([O-])([O-])=O.[Na+].[Na+].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9](B(O)O)[CH:8]=1.Br[C:17]1[CH:26]=[CH:25][C:20]([CH:21]=[CH:22][CH:23]=[O:24])=[CH:19][CH:18]=1>CO.C1(C)C=CC=CC=1.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:17]2[CH:26]=[CH:25][C:20](/[CH:21]=[CH:22]/[CH:23]=[O:24])=[CH:19][CH:18]=2)[CH:8]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 5151110HCID 5151110、化合物

生成物 1

HCID 22630906(E)-3-[4-(3-Pyridinyl)phenyl]-2-propenal

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

2M aq. Na2CO3 (1 mL) and a solution of 3-pyridinylboronic acid (148 mg, 1.20 mmol) in methanol (1 mL) were added to a solution of 4-bromocinnamaldehyde (211 mg, 1.00 mmol, prepared as described in Tetrahedron 1998, 54, 10761) and tetrakis(triphenylphosphine)palladium(0) (35 mg, 0.030 mmol) in toluene (2 mL) and the mixture was heated to reflux for 36 h. The cooled reaction mixture was diluted with dichloromethane, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 1:1 hexane/ethyl acetate) yielded the title compound. MS 210 (M+H)+.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 36 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, 1:1 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-e324611707d74566ad3fd3dc22355c6b
出典データセット
uspto-grants-2004_11
特許番号
US06825170B2

反応ノート

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