Hydrochloric Acid → HCID 57615034, compound

HRID 2390959Notes

Reaction equation

HRID 2390959 reaction equation
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.CCCCCC.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:27]1[CH:28]=[CH:29][C:30]2[S:34][CH:33]=[CH:32][C:31]=2[CH:35]=1.[C:36]([O:44][CH2:45][CH3:46])(=[O:43])[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].Cl>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O.COCCOC>[S:34]1[C:30]2[CH:29]=[CH:28][C:27]([CH:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:36]([O:44][CH2:45][CH3:46])=[O:43])=[CH:35][C:31]=2[CH:32]=[CH:33]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 10796Cesium carbonateHCID 27765785-Bromo-1-benzothiopheneHCID 86628723Tri(tert-butyl)phosphine hexane

Product 1

HCID 57615034HCID 57615034, compoundYield 100.6%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1,2-dimethoxyethane (10 mL) suspension of 0.02 g of tris(dibenzylideneacetone)dipalladium(0) were added 0.11 g of 10% (w/w) tri(tert-butyl)phosphine/hexane, 1.76 g of cesium carbonate, 0.50 g of 5-bromobenzothiophene and 0.45 g of diethyl malonate, which was then refluxed for 2 hours. To the reaction mixture were added water and ethyl acetate, followed by adjustment to pH2 using 2 mol/L hydrochloric acid. The organic layer was separated, and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; hexane:ethyl acetate=10:1) to provide 0.69 g of diethyl 2-(1-benzothiophen-5-yl)malonate as white solid form.

Workup

  1. temperaturewas then refluxed for 2 hours
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationby distilling off the solvent under reduced pressure
  5. customThe resultant residue was purified

Sources & evidence

ORD record
ord-668dee67ecba4688a987f89563180438
Source dataset
uspto-grants-2012_09
Patent number
US08273902B2

Reaction notes

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