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Water → 5-[2-[4-(Dibutylamino)phenyl]vinyl]thiophene-2-carboaldehyde

HRID 85341
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HRID 85341 반응식
[CH2:1]([N:5]([CH2:19][CH2:20][CH2:21][CH3:22])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C([Li])CCC.CN(C)[CH:30]=[O:31].O>O1CCCC1>[CH2:19]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[S:15][C:16]([CH:30]=[O:31])=[CH:17][CH:18]=2)=[CH:8][CH:7]=1)[CH2:20][CH2:21][CH3:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 68008974Dibutyl[4-[2-(thiophene-2-yl)vinyl]phenyl]amineHCID 178418339Butyllithium

생성물 1

HCID 765636755-[2-[4-(Dibutylamino)phenyl]vinyl]thiophene-2-carboaldehyde수율 95.5%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

In a stream of argon, in tetrahydrofuran was dissolved 3.0 g (0.97 mmol) of dibutyl[4-[2-(thiophene-2-yl)vinyl]phenyl]amine. To this mixture, 9.0 ml of n-butyllithium (1.6 M solution in hexane) (14.4 mmol) was added dropwise under cooling. After the mixture was stirred for 1 hour, 0.87 g (11.9 mmol) of N,N-dimethylformamide was added dropwise thereto. After 20 minutes, the temperature was allowed to rise and 30 ml of water was added dropwise. Tetrahydrofuran was evaporated off. Extraction with chloroform, drying over anhydrous sodium sulfate, and concentration were performed. The residual liquid was purified by silica gel column chromatography to give 3.12 g of a reddish orange oily matter (yield: 95.5%).

후처리

  1. temperatureunder cooling
  2. waitAfter 20 minutes
  3. customTetrahydrofuran was evaporated off
  4. extractionExtraction with chloroform
  5. dry with materialdrying over anhydrous sodium sulfate, and concentration
  6. customThe residual liquid was purified by silica gel column chromatography
  7. customto give 3.12 g of a reddish orange oily matter (yield: 95.5%)

출처 및 근거

ORD 기록
ord-3a2d3b8c0c4c44e29c7a2428cd33656b
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846955B2

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