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

HRID 1835469

反応式

HRID 1835469 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 1509652,2'-Bithiophene-5-carboxylic acid収率 75.6%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-60 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-1818d00f6c8f4f73891ffaf279776cd8
出典データセット
uspto-grants-2004_08
特許番号
US06770667B1

関連ノート

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