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Ethyl cyanoacetate → Benzo[b]thiophene-5-acetic acid

HRID 553209
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 553209
CC(C)([O-])C.[K+].[C:7]([CH2:9][C:10]([O:12]CC)=[O:11])#N.BrC1[CH:17]=[CH:18][C:19]2[S:23][CH:22]=[CH:21][C:20]=2[CH:24]=1.[OH-].[Na+]>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.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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[BH4-].[Na+].O.C(O)C.C1(C)C=CC=CC=1>[S:23]1[C:19]2[CH:18]=[CH:17][C:7]([CH2:9][C:10]([OH:12])=[O:11])=[CH:24][C:20]=2[CH:21]=[CH:22]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

12

Edukt 4

HCID 7764Ethyl cyanoacetateHCID 14798Sodium Hydroxide2×HCID 27765785-Bromo-1-benzothiopheneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 11469582Benzo[b]thiophene-5-acetic acidAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 7

HCID 11776
Triphenylphosphine
Katalysator
HCID 4311764Sodium borohydrideKatalysator
HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel2×
HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To toluene (25 mL) suspension of 0.16 g of dichlorobis(triphenylphosphine)palladium(II) were added 0.12 g of triphenylphosphine, 0.01 g of sodium borohydride, 5.79 g of potassium tert-butoxide and 2.92 g of ethyl cyanoacetate, which was then stirred at room temperature for 10 minutes. Thereto were added 5.00 g of 5-bromobenzothiophene and 25 mL of toluene, which was then refluxed for 4 hours. Thereto was added 0.14 g of tetrakis(triphenylphosphine)palladium(0), which was then refluxed for 2 hours. Next, to the reaction solution were added 25 mL of ethanol, 2.82 g of sodium hydroxide and 5 mL of water, which was then refluxed for 6 hours. Thereto was added 2.82 g of sodium hydroxide, which was then refluxed for 5 hours. To the reaction mixture were added 15 mL of water and 0.5 g of activated carbon, and insoluble matter was filtered off. The aqueous layer was separated, and to the solution was added 35 mL of ethanol. The pH was adjusted to 2 with 15 mL of hydrochloric acid. Thereto was added 15 mL of water, which was then stirred at 40° C. Thereto was added 30 mL of water, which was stirred. After that, it was cooled. The precipitate was collected by filtration to provide 3.38 g of 2-(1-benzothiophen-5-yl)acetic acid as pale yellow solid form.

Aufarbeitung

  1. temperaturewas then refluxed for 4 hours
  2. temperaturewas then refluxed for 2 hours
  3. temperaturewas then refluxed for 6 hours
  4. temperaturewas then refluxed for 5 hours
  5. filtrationwas filtered off
  6. customThe aqueous layer was separated
  7. additionto the solution was added 35 mL of ethanol
  8. additionThereto was added 15 mL of water, which
  9. stirringwas then stirred at 40° C
  10. additionThereto was added 30 mL of water, which
  11. stirringwas stirred
  12. temperatureAfter that, it was cooled
  13. filtrationThe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-c046c94abaaf45e5aa5bbd24642565e9
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07951963B2

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