Water → 5-(4-Dibutylamino-2-methoxyphenyl)-2,4-pentadienenitrile

HRID 85281ノート

反応式

HRID 85281 の反応式
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH2:14]([N:18]([CH2:31][CH2:32][CH2:33][CH3:34])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][CH:27]=O)=[C:21]([O:29][CH3:30])[CH:20]=1)[CH2:15][CH2:16][CH3:17].O>O1CCCC1>[CH2:14]([N:18]([CH2:31][CH2:32][CH2:33][CH3:34])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][CH:27]=[CH:5][C:3]#[N:4])=[C:21]([O:29][CH3:30])[CH:20]=1)[CH2:15][CH2:16][CH3:17]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 866675703-(4-Dibutylamino-2-methoxyphenyl)propenal

生成物 1

HCID 866675735-(4-Dibutylamino-2-methoxyphenyl)-2,4-pentadienenitrile収率 91.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To 200 mg (8.3 mmol) of sodium hydride, 14 ml of tetrahydrofuran was added. To this mixture, 1.47 g (8.3 mmol) of diethyl cyanomethylphosphonate was added dropwise under ice cooling, and the mixture was stirred for 20 minutes. Next, 1.02 g (3.52 mmol) of 3-(4-dibutylamino-2-methoxyphenyl)propenal in tetrahydrofuran was added dropwise. After stirred for 30 minutes, the reaction mixture was poured into 100 ml of water and subjected to extraction with ethyl acetate. The extract was washed with a saturated saline solution, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give 1.0 g of an orange oily matter (yield: 91.2%).

後処理

  1. stirringAfter stirred for 30 minutes
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe extract was washed with a saturated saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. customto give 1.0 g of an orange oily matter (yield: 91.2%)

出典と根拠

ORDレコード
ord-0532b1d1a0b946a991e148c549f7de82
出典データセット
uspto-grants-2014_09
特許番号
US08846955B2

反応ノート

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