Methyl vinyl ketone → 9-Carbamoyl-9-(3-oxobutyl)fluorene

HRID 542639

反応式

HRID 542639 の反応式
[C:1]([CH:4]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[CH:29]([C:31]([CH3:33])=[O:32])=[CH2:30]>O1CCCC1>[C:1]([C:4]1([CH2:30][CH2:29][C:31](=[O:32])[CH3:33])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=[O:3])[NH2:2]

参加物

5

反応物 3

HCID 6570Methyl vinyl ketoneHCID 66854Benzyltrimethylammonium hydroxideHCID 3450289H-fluorene-9-carboxamide

生成物 1

HCID 138534889-Carbamoyl-9-(3-oxobutyl)fluorene

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

To a stirred warm (45° C.) solution of 62.7 g. (0.3 mole) of 9-carbamoylfluorene in 700 ml. of tetrahydrofuran were added in one portion 30 ml. of a 40% aqueous solution of benzyltrimethylammonium hydroxide. The reaction mixture was stirred at 45° C. for fifteen minutes, and was then diluted by dropwise addition of 24.5 g. (0.35 mole) of methyl vinyl ketone. The reaction mixture was heated at reflux for three hours following complete addition, and then it was cooled to about 30° C. and added to 500 g. of ice. The aqueous reaction mixture was extracted several times with 50% diethyl ether in ethyl acetate, and the extracts were combined, washed with water, with 10% aqueous sodium hydroxide, again with water and then dried. Removal of the solvent by evaporation under reduced pressure afforded a solid which, following crystallization from ethyl acetate, was identified as 46.1 g. of 9-carbamoyl-9-(3-oxobutyl)fluorene. m.p. 125°-128° C.

後処理

  1. additionwas then diluted by dropwise addition of 24.5 g
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for three hours
  4. additionaddition
  5. temperatureit was cooled to about 30° C.
  6. additionadded to 500 g
  7. extractionThe aqueous reaction mixture was extracted several times with 50% diethyl ether in ethyl acetate
  8. washwashed with water, with 10% aqueous sodium hydroxide, again with water
  9. customdried
  10. customRemoval of the solvent
  11. customby evaporation under reduced pressure
  12. customafforded a solid which
  13. customcrystallization from ethyl acetate

出典と根拠

ORDレコード
ord-78b2e50548b7400f8b7e73a040a3fcf4
出典データセット
uspto-grants-1987_04
特許番号
US04658061

関連ノート

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