Tetrabutylammonium Fluoride → Tert-butyl 2-[(4-ethynylphenyl)acetyl]hydrazinecarboxylate

HRID 1465431ノート

反応式

HRID 1465431 の反応式
C[Si]([C:5]#[C:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])=[CH:9][CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:6]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([NH:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[O:15])=[CH:9][CH:8]=1)#[CH:5]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 67266446Tert-butyl 2-({4-[(trimethylsilyl)ethynyl]phenyl}acetyl)hydrazinecarboxylate

生成物 1

HCID 86651837Tert-butyl 2-[(4-ethynylphenyl)acetyl]hydrazinecarboxylate収率 96%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of tert-butyl 2-({4-[(trimethylsilyl)ethynyl]phenyl}acetyl)hydrazinecarboxylate (10.1 g, 29.4 mmol) in anhydrous tetrahydrofuran (150 ml) was added at 0° C. tetra-n-butylammonium fluoride (1M tetrahydrofuran solution, 29.4 ml, 29.4 mmol). After stirring at 0° C. for 45 mins, the mixture was concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with ethyl acetate, and the extract was concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to give tert-butyl 2-[(4-ethynylphenyl)acetyl]hydrazinecarboxylate (7.7 g, yield 96%) as a yellow solid.

後処理

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. concentrationthe extract was concentrated under reduced pressure
  5. customThe concentrated residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

出典と根拠

ORDレコード
ord-6994e59836124459a8ef6dd20e9ad3e5
出典データセット
uspto-grants-2015_04
特許番号
US08999989B2

反応ノート

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