Hydrochloric Acid → HCID 59506249, compound

HRID 1098768Notes

Reaction equation

HRID 1098768 reaction equation
[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]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 1069780HCID 1069780, compoundHCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)ethene

Product 1

HCID 59506249HCID 59506249, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-91e1dc184cd54f02baf052f2a209591c
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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