2,3-Dimethyl-1,3-butadiene → 4-(4,5-Dimethylcyclohexa-1,4-dienyl)butan-1-ol

HRID 1398059

반응식

HRID 1398059 반응식
[CH3:1][C:2]([C:4]([CH3:6])=[CH2:5])=[CH2:3].[CH2:7]([OH:13])[CH2:8][CH2:9][CH2:10][C:11]#[CH:12]>C1COCC1.[Co](Br)Br.[I-].[Zn+2].[I-].[Zn].C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:3][C:2]1[CH2:1][CH:12]=[C:11]([CH2:10][CH2:9][CH2:8][CH2:7][OH:13])[CH2:5][C:4]=1[CH3:6]

참가 물질

8

반응물 2

HCID 105662,3-Dimethyl-1,3-butadieneHCID 702345-Hexyn-1-ol

생성물 1

HCID 675060094-(4,5-Dimethylcyclohexa-1,4-dienyl)butan-1-ol수율 63.8%

시약·촉매·용매 5

HCID 23994Zinc촉매HCID 24610Cobalt dibromide촉매HCID 742671,2-Bis(diphenylphosphino)ethane촉매HCID 9883512zinc(II)iodide촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

In 40 mL of THF, 1,2-bis(diphenylphosphino)ethane (800 mg, 2.00 mmol), cobalt bromide (437 mg, 2.00 mmol), zinc iodide (1.28 g, 4.00 mmol), and zinc (260 mg, 4.00 mmol) were dissolved, followed by stirring at 70° C. for 15 minutes. After cooling to room temperature, 2,3-dimethyl-1,3-butadiene (9.86 g, 120 mmol) was added. Then, 5-hexyn-1-ol (9.8 g, 100 mmol) was slowly added dropwise with cooling in a water bath. After stirring at 35° C. for 1 hour, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1). Thus, 11.5 g of the title compound, an alcohol, was obtained as a colorless oily substance. Yield: 63.4%.

후처리

  1. temperatureAfter cooling to room temperature
  2. temperaturewith cooling in a water bath
  3. stirringAfter stirring at 35° C. for 1 hour
  4. customthe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1)

출처 및 근거

ORD 기록
ord-9cf249840b7f453ba9e9e3c072347649
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901323B2

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