Hydrochloric Acid → HCID 57615038, compound

HRID 553208Notes

Reaction equation

HRID 553208 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].CC(C)([O-])C.[K+].Br[C:16]1[CH:17]=[CH:18][C:19]2[S:23][CH:22]=[CH:21][C:20]=2[CH:24]=1.Cl>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.C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[S:23]1[C:19]2[CH:18]=[CH:17][C:16]([CH:3]([C:1]#[N:2])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[CH:24][C:20]=2[CH:21]=[CH:22]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 27765785-Bromo-1-benzothiopheneHCID 23665647Potassium tert-butoxide

Product 1

HCID 57615038HCID 57615038, compoundYield 46.3%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To toluene (3 mL) solution of 0.21 g of ethyl cyanoacetate were added 0.41 g of potassium tert-butoxide, 0.30 g of 5-bromobenzothiophene and 0.02 g of tetrakis(triphenylphosphine)palladium(0), which was then refluxed for 7.5 hours. To the reaction mixture was added water, and the pH was adjusted to 2 with hydrochloric acid. Thereto was added ethyl acetate, and insoluble matter was filtered off. The organic layer was separated, washed with water, 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=5:1) to provide 0.16 g of ethyl 2-(1-benzothiophen-5-yl)-2-cyanoacetate as pale yellow solid form.

Workup

  1. temperaturewas then refluxed for 7.5 hours
  2. filtrationwas filtered off
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe resultant residue was purified

Sources & evidence

ORD record
ord-78ae0da145b348ea84233db0395796a4
Source dataset
uspto-grants-2011_05
Patent number
US07951963B2

Reaction notes

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