Hydrochloric Acid → HCID 86610996, 화합물

HRID 970942노트

반응식

HRID 970942 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 86610996HCID 86610996, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ab306f781d844f5bc89967bb4fb4c7a
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312283B2

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