Hydrochloric Acid → HCID 86610996, compound

HRID 970942Notes

Reaction equation

HRID 970942 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 86610996HCID 86610996, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8ab306f781d844f5bc89967bb4fb4c7a
Source dataset
uspto-grants-2007_12
Patent number
US07312283B2

Reaction notes

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