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

HRID 553209
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HRID 553209 반응식
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
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참가 물질

12

반응물 4

HCID 7764Ethyl cyanoacetateHCID 14798Sodium Hydroxide2회HCID 27765785-Bromo-1-benzothiopheneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 11469582Benzo[b]thiophene-5-acetic acid수율 74.9%

시약·촉매·용매 7

HCID 11776Triphenylphosphine
촉매
HCID 4311764Sodium borohydride촉매
HCID 178418397HCID 178418397, 화합물촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 702Ethanol용매
HCID 962Water용매2회
HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c046c94abaaf45e5aa5bbd24642565e9
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07951963B2

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