Dimethylformamide → HCID 86667592, compound

HRID 85302Notes

Reaction equation

HRID 85302 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[C:4]=1[CH:13]=[CH:14][C:15]1[S:16][CH:17]=[CH:18][CH:19]=1.C([Li])CCC.CN(C)[CH:27]=[O:28]>O1CCCC1>[CH3:12][O:11][C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[CH:13]=[CH:14][C:15]1[S:16][C:17]([CH:27]=[O:28])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 680086492-[2-(2,4,6-Trimethoxyphenyl)vinyl]thiopheneHCID 178418339Butyllithium

Product 1

HCID 86667592HCID 86667592, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of argon, in 10 ml of tetrahydrofuran was dissolved 500 mg (1.80 mmol) of 2-[2-(2,4,6-trimethoxyphenyl) 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 1 hour. To this mixture, 0.16 ml (2.00 mmol) of N,N-dimethylformamide was added dropwise and reacted. After reacted at gradually increasing temperature, the reaction mixture was stirred at room temperature for 12 hours. The mixture was poured into 50 ml of ice water and subjected to 3 times of extraction with 200 ml of chloroform. The extract was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel chromatography to give 380 mg (yield: 69%) of 5-[2-(2,4,6-trimethoxyphenyl)vinyl]thiophene-2-carbaldehyde as a light yellow crystal.

Workup

  1. additionwas added dropwise
  2. temperatureunder cooling
  3. customreacted
  4. customAfter reacted
  5. temperatureat gradually increasing temperature
  6. stirringthe reaction mixture was stirred at room temperature for 12 hours
  7. extractionsubjected to 3 times of extraction with 200 ml of chloroform
  8. washThe extract was washed with a saturated saline solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-164844acd6aa4571a597f497d27f098d
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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