Acetic Acid → 3-Oxo-2-[(9-oxo-9H-fluoren-4-yl)methylene]butanenitrile

HRID 1951379ノート

反応式

HRID 1951379 の反応式
[C:1]([CH:3]=[C:4]([O-:6])[CH3:5])#[N:2].[Na+].[O:8]=[C:9]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:22]=O)[C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2.C(O)(=O)C.N1CCCCC1>ClCCl>[O:6]=[C:4]([CH3:5])[C:3](=[CH:22][C:17]1[C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:8])[C:21]=2[CH:20]=[CH:19][CH:18]=1)[C:1]#[N:2]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 113332519-Oxo-9H-fluorene-4-carbaldehydeHCID 74083625Sodium 1-cyanoprop-1-en-2-olate

生成物 1

HCID 674179733-Oxo-2-[(9-oxo-9H-fluoren-4-yl)methylene]butanenitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

The compound from example 11A (5.21 g, 25.0 mmol) is introduced into 180 ml of dichloromethane, and the compound from example 20A (2.89 g, 27.5 mmol), acetic acid (1.72 ml, 30.0 mmol) and piperidine (0.25 ml, 2.50 mmol) are added. The mixture is stirred at the boiling point with a water trap for 4 h. Cooling to RT is followed by dilution with 30 ml of dichloromethane and washing with water (2×50 ml), the organic phase is dried over sodium sulfate and the solvent is removed in a rotary evaporator. The resulting crude product is purified by chromatography on silica gel 60 with dichloromethane as mobile phase. Combining the product fractions and removing the solvent results in 5.40 g (79% of theory) of the title compound as mixture of E/Z isomers.

後処理

  1. washwashing with water (2×50 ml)
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. customthe solvent is removed in a rotary evaporator
  4. customThe resulting crude product is purified by chromatography on silica gel 60 with dichloromethane as mobile phase
  5. customremoving the solvent

出典と根拠

ORDレコード
ord-bdae7f54926e42d1a67f1fdf84f4d451
出典データセット
uspto-grants-2013_03
特許番号
US08404709B2

反応ノート

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