Hydrochloric Acid → HCID 86610996、化合物

HRID 970942ノート

反応式

HRID 970942 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 86610996HCID 86610996、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8ab306f781d844f5bc89967bb4fb4c7a
出典データセット
uspto-grants-2007_12
特許番号
US07312283B2

反応ノート

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