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

HRID 85301

Reaktionsgleichung

Reaktionsgleichung von HRID 85301
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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 680086492-[2-(2,4,6-Trimethoxyphenyl)vinyl]thiopheneAusbeute 92,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-aaf7754e66d54ee3b720359ff69a7970
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846955B2

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