Chloroform → HCID 86667594, compound

HRID 85306Notes

Reaction equation

HRID 85306 reaction equation
[CH2:1]([N:5]([CH2:23][CH2:24][CH2:25][CH3:26])[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([CH:14]=[CH:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[C:8]([O:21][CH3:22])[CH:7]=1)[CH2:2][CH2:3][CH3:4].C([Li])CCC.CN(C)[CH:34]=[O:35].C(Cl)(Cl)Cl>O1CCCC1>[CH2:23]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]1[CH:7]=[C:8]([O:21][CH3:22])[C:9]([CH:14]=[CH:15][C:16]2[S:17][C:18]([CH:34]=[O:35])=[CH:19][CH:20]=2)=[C:10]([O:12][CH3:13])[CH:11]=1)[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 680091252-[2-(4-Dibutylamino-2,6-dimethoxyphenyl)vinyl]thiopheneHCID 178418339Butyllithium

Product 1

HCID 86667594HCID 86667594, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of argon, in 10 ml of tetrahydrofuran was dissolved 0.75 g (2.00 mmol) of 2-[2-(4-dibutylamino-2,6-dimethoxyphenyl)vinyl]thiophene, and 1.27 ml of n-butyllithium (1.6 M solution in hexane) (2.03 mmol) was added dropwise thereto under cooling. The mixture was stirred for hour. To this mixture, 0.20 ml (1.20 mmol) of N,N-dimethylformamide was added dropwise and reacted. The temperature was then allowed to rise gradually, and the mixture was allowed to react at room temperature for 12 hours. After the mixture was poured into 100 ml of ice water, extraction with 200 ml of chloroform, washing with a saturated saline solution, drying over anhydrous magnesium sulfate, and concentration were performed. The residue was purified by silica gel chromatography to give 482 mg (yield: 60%) of 5-[2-(4-dibutylamino-2,6-dimethoxyphenyl)vinyl]thiophene-2-carboaldehyde as a dark purple crystal (mp: 105-106° C.).

Workup

  1. additionwas added dropwise
  2. temperatureunder cooling
  3. customreacted
  4. customto react at room temperature for 12 hours
  5. washwashing with a saturated saline solution
  6. dry with materialdrying over anhydrous magnesium sulfate, and concentration
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a8d851bf55f849deb394a37c85cc55d6
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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