Acetic Acid → 1-(prop-2-en-1-yl)-1H-1,3-benzodiazole-2-carbaldehyde

HRID 2231235ノート

反応式

HRID 2231235 の反応式
[CH2:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3].C([Li])CCC.[CH:18](OCC)=[O:19].C(O)(=O)C>O1CCCC1.CCCCCC>[CH2:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[CH:18]=[O:19])[CH:2]=[CH2:3]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 8025Ethyl formateHCID 5941171-AllylbenzimidazoleHCID 178418339Butyllithium

生成物 1

HCID 9625211-(prop-2-en-1-yl)-1H-1,3-benzodiazole-2-carbaldehyde

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-20 °C

実験手順

To a solution of 10 g (0.053 mole) of 1-allylbenzimidazole in 75 ml of tetrahydrofuran cooled to -78° C. was added 20.68 ml (0.053 mole) of 2.6M n-butyllithium in hexane over a period of 15 minutes. After 30 minutes of stirring 4.28 ml (0.053 mole) of ethyl formate was added and the reaction allowed to stir for one hour. Acetic acid (3.03 ml, 0.053 mole) was added, the cooling bath removed and the mixture allowed to warm to -20° C. The mixture was poured into water and the product extracted (3×100 ml) with ethyl acetate. The extracts were combined, dried over magnesium sulfate and concentrated to a brown oil which was chromatographed on 350 g of silica gel using ethyl acetate-chloroform as the eluent, 2.3 g.

後処理

  1. additionwas added
  2. customthe cooling bath removed
  3. additionThe mixture was poured into water
  4. extractionthe product extracted (3×100 ml) with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to a brown oil which
  7. customwas chromatographed on 350 g of silica gel

出典と根拠

ORDレコード
ord-370b222dd28145c58223e588287097fa
出典データセット
uspto-grants-1988_11
特許番号
US04782050

反応ノート

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