Carbon Dioxide → 2,2'-Bithiophene-5-carboxylic acid

HRID 1835469

반응식

HRID 1835469 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.C([Li])CCC.[C:16](=[O:18])=[O:17].Cl>O1CCCC1.CCCCCC.C(OCC)(=O)C>[S:1]1[C:5]([C:16]([OH:18])=[O:17])=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1

참가 물질

8

반응물 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 681202,2'-BithiopheneHCID 178418339Butyllithium

생성물 1

HCID 1509652,2'-Bithiophene-5-carboxylic acid수율 75.6%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-60 °C

실험 절차

To a suspension of 2,2′-bithiophene (1.0 g) in tetrahydrofuran (10 ml) was added a solution of n-butyl lithium in n-hexane (1.54 M, 4.3 ml) at −25° C. under nitrogen atmosphere. The mixture was stirred at −60° C. for 30 minutes. To the solution dry-ice (1.0 g) was added and the mixture was stirred at ambient temperature for 30 minutes. To the resultant suspension hydrochloric acid (1N, 10 ml) and ethyl acetate were added. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether. The resulting precipitate was collected by filtration, washed with diisopropyl ether and dried to give [2,2′]bithiophenyl-5-carboxylic acid (952 mg, 75.6%).

후처리

  1. stirringthe mixture was stirred at ambient temperature for 30 minutes
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with diisopropyl ether
  6. filtrationThe resulting precipitate was collected by filtration
  7. washwashed with diisopropyl ether
  8. customdried

출처 및 근거

ORD 기록
ord-1818d00f6c8f4f73891ffaf279776cd8
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06770667B1

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