Water → 3-[5-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]acrylonitrile

HRID 85290노트

반응식

HRID 85290 반응식
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH2:14]([N:18]([CH2:36][CH2:37][CH2:38][CH3:39])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][C:27]2[S:31][C:30]([CH:32]=O)=[CH:29][CH:28]=2)=[C:21]([O:34][CH3:35])[CH:20]=1)[CH2:15][CH2:16][CH3:17].O>O1CCCC1>[CH2:14]([N:18]([CH2:36][CH2:37][CH2:38][CH3:39])[C:19]1[CH:24]=[CH:23][C:22]([CH:25]=[CH:26][C:27]2[S:31][C:30]([CH:32]=[CH:5][C:3]#[N:4])=[CH:29][CH:28]=2)=[C:21]([O:34][CH3:35])[CH:20]=1)[CH2:15][CH2:16][CH3:17]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 866675385-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-carboaldehyde

생성물 1

HCID 680092803-[5-[2-(4-Dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-yl]acrylonitrile수율 90.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To 111 mg (4.63 mmol) of sodium hydride, 8 ml of tetrahydrofuran was added. To this mixture, 820 mg (4.63 mmol) of diethyl cyanomethylphosphonate was added dropwise under ice cooling, and the mixture was stirred for 30 minutes. Next, 860 mg (2.31 mmol) of 5-[2-(4-dibutylamino-2-methoxyphenyl)vinyl]thiophene-2-carboaldehyde in tetrahydrofuran was added dropwise, and the mixture was stirred for 1 hour. The reaction mixture was poured into 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 828 mg of a deep red oily matter (yield: 90.7%).

후처리

  1. stirringthe mixture was stirred for 1 hour
  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 828 mg of a deep red oily matter (yield: 90.7%)

출처 및 근거

ORD 기록
ord-f71b300b87df400391f69adfa468627c
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846955B2

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