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

HRID 553209
ノート
印刷プレビュー

反応式

HRID 553209 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

12

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 7

HCID 11776Triphenylphosphine
触媒
HCID 4311764Sodium borohydride触媒
HCID 178418397HCID 178418397、化合物触媒
HCID 178418476HCID 178418476、化合物触媒
HCID 702Ethanol溶媒
HCID 962Water溶媒2 回
HCID 1140Toluene溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c046c94abaaf45e5aa5bbd24642565e9
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07951963B2

反応ノート

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