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

HRID 85341
ノート
印刷プレビュー

反応式

HRID 85341 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

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%).

後処理

  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%)

出典と根拠

ORDレコード
ord-3a2d3b8c0c4c44e29c7a2428cd33656b
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846955B2

反応ノート

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