Ethyl Acetate → 5-Vinylnicotinonitrile

HRID 606827

反応式

HRID 606827 の反応式
[CH2:1]([Sn](CCCC)(CCCC)C=C)[CH2:2]CC.Br[C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH:24]=1)[C:22]#[N:23].[Cl-].[NH4+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]([C:17]1[CH:18]=[N:19][CH:20]=[C:21]([CH:24]=1)[C:22]#[N:23])=[CH2:2]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 81998TributylvinyltinHCID 7367935-Bromonicotinonitrile

生成物 1

HCID 670475755-Vinylnicotinonitrile収率 70.3%

試薬・触媒・溶媒 2

HCID 178419050HCID 178419050、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

Add bis(triphenylphosphine)palladium (II) dichloride (0.460 g, 0.66 mmol) and tributyl-vinyl-stannane (7.2 mL, 24.6 mmol) to a solution of 5-bromonicotinonitrile (3.0 g, 16.4 mmol) in toluene (50 mL) and stir at 110° C. for 150 min. Add an aqueous saturated solution of ammonium chloride and ethyl acetate and separate the layers. Wash the organic layer twice with an aqueous saturated solution of potassium fluoride and once with water. Dry (sodium sulfate), filter, and concentrate. Purify the residue by silica gel chromatography, eluting with 3:1 hexane:ethyl acetate, to give the title compound (1.5 g, 70%).

後処理

  1. customseparate the layers
  2. washWash the organic layer twice with an aqueous saturated solution of potassium fluoride
  3. dry with materialDry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with 3:1 hexane

出典と根拠

ORDレコード
ord-56b43414d3494c388f5d80d9389fb119
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

関連ノート

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