Hydrochloric Acid → HCID 59506249、化合物

HRID 1098768ノート

反応式

HRID 1098768 の反応式
[Br:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[CH:4][C:3]=1[S:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)(=[O:11])=[O:10].[CH2:18]([O:20]C=C[Sn](CCCC)(CCCC)CCCC)[CH3:19].Cl.C([O-])(O)=O.[Na+]>C(#N)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([C:18](=[O:20])[CH3:19])[CH:5]=[CH:4][C:3]=1[S:9]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)(=[O:11])=[O:10]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 1069780HCID 1069780、化合物HCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)ethene

生成物 1

HCID 59506249HCID 59506249、化合物収率 68%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of the product obtained in step 1 (4.8 g, 12.5 mmol) in ACN (15 ml) was added Cul (119 mg, 0.62 mmol), PdCl2(PPh3)2 and 1-(ethoxyvinyl)tributyl-stannane (5.4 g, 14.95 mmol). The mixture was refluxed for 3 h. After cooling, the reaction mixture was acidified with 1 N HCl (7 ml) and stirred for 20 min. The reaction mixture was neutralized with saturated aqueous NaHCO3 and extracted with AcOEt. The organic phase was dried over Na2SO4 and evaporated. Purification of the crude product by silica gel chromatography using ethyl acetate/n-heptane gave the desired product (2.95 g, 68%).

後処理

  1. temperatureThe mixture was refluxed for 3 h
  2. temperatureAfter cooling
  3. extractionextracted with AcOEt
  4. dry with materialThe organic phase was dried over Na2SO4
  5. customevaporated
  6. customPurification of the crude product by silica gel chromatography

出典と根拠

ORDレコード
ord-91e1dc184cd54f02baf052f2a209591c
出典データセット
uspto-grants-2012_03
特許番号
US08143242B2

反応ノート

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