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

HRID 85341Notes

Reaction equation

HRID 85341 reaction equation
[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]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 68008974N,N-Dibutyl-4-[2-(2-thienyl)ethenyl]benzenamineHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-3a2d3b8c0c4c44e29c7a2428cd33656b
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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