Hydrochloric Acid → HCID 86610996, Verbindung

HRID 970942

Reaktionsgleichung

Reaktionsgleichung von HRID 970942
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11](=O)[CH2:12][CH2:13][CH:14]=[CH2:15].C1COCC1.[CH:22]1([Mg]Cl)[CH:26]=[CH:25][CH:24]=[CH:23]1.Cl>O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH2:12][CH2:13][CH:14]=[CH2:15])=[C:22]1[CH:26]=[CH:25][CH:24]=[CH:23]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 112412734-Penten-1-one, 1-(2-naphthalenyl)-HCID 178478988HCID 178478988, Verbindung

Produkt 1

HCID 86610996HCID 86610996, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

First, 6-(2-naphthyl)-6-(3-butenyl)fulvene was prepared from cyclopentadienyl Grignard reagents as follows. A 1 L round bottomed flask was charged with 1-(2-naphthyl)-4-penten-1-one, 97% (21.73 g, 100 mmol), THF (100 mL), and a stir bar, and cooled in an ice bath. Cyclopentadienyl magnesium chloride (150 mL of approximately 1 M solution in THF, 330 mmol) was added dropwise over ½ hour. The yellow solution was stirred for 2 hours in the ice bath. The yellow solution was then refluxed for 2.5 hours, during which time a red color developed. The solution was acidified by first adding 100 mLs of water, and then adding 100 mL of 1 M HCl. The product was extracted with pentane, and the pentane extracts were collected, washed with water, and dried over sodium sulfate. Elution through silica with pentane and concentration under vacuum afforded 20.25 g (73%) of the product 6-(2-naphthyl)-6-(3-butenyl)fulvene as a red oil, which was 93% pure. The major impurity was dicyclopentadiene.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. temperatureThe yellow solution was then refluxed for 2.5 hours, during which time a red color
  3. extractionThe product was extracted with pentane
  4. customthe pentane extracts were collected
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. washElution through silica
  8. concentrationwith pentane and concentration under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-8ab306f781d844f5bc89967bb4fb4c7a
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312283B2

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