Chloroform → 2-[2-(2,4,6-Trimethoxyphenyl)vinyl]thiophene

HRID 85301Notes

Reaction equation

HRID 85301 reaction equation
C1([Li])C=CC=CC=1.[Br-].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:34][O:35][C:36]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[C:40]([O:46][CH3:47])[C:37]=1[CH:38]=O.C(Cl)(Cl)Cl>O1CCCC1>[CH3:34][O:35][C:36]1[CH:43]=[C:42]([O:44][CH3:45])[CH:41]=[C:40]([O:46][CH3:47])[C:37]=1[CH:38]=[CH:14][C:10]1[S:9][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 700192,4,6-TrimethoxybenzaldehydeHCID 10741697Triphenyl(2-thienylmethyl)phosphonium BromideHCID 178506676HCID 178506676, compound

Product 1

HCID 680086492-[2-(2,4,6-Trimethoxyphenyl)vinyl]thiopheneYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a stream of argon, to 30 ml of tetrahydrofuran was added 0.95 g of phenyllithium (19% solution in dibutylether) (2.15 mmol). To this mixture, 0.78 g (1.98 mmol) of thiophene-2-ylmethyltriphenylphosphonium bromide was added under cooling. After the mixture was well-stirred, 0.38 g (1.98 mmol) of 2,4,6-trimethoxybenzaldehyde dissolved in 3 ml of tetrahydrofuran was added dropwise. The mixture was reacted with stirring for 1.5 hours. After the reaction mixture was poured into 70 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 508 mg (yield: 92%) of 2-[2-(2,4,6-trimethoxyphenyl)vinyl]thiophene as a colorless crystal.

Workup

  1. temperatureunder cooling
  2. additionwas added dropwise
  3. customThe mixture was reacted
  4. stirringwith stirring for 1.5 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-aaf7754e66d54ee3b720359ff69a7970
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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