Isoprene → 11,11-Diphenylundec-1-ene

HRID 273823노트

반응식

HRID 273823 반응식
[Li].[C:2]1([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(OC)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=CC(=C)C.[Cl-].[NH4+]>N.C1COCC1.CO>[C:2]1([CH:8]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 6557IsopreneHCID 25517Ammonium ChlorideHCID 3028194Lithium2회HCID 2008832511,11-Diphenyl-11-methoxyundec-1-ene

생성물 1

HCID 2008832411,11-Diphenylundec-1-ene수율 105.4%

시약·촉매·용매 3

HCID 222Ammonia용매2회HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

Lithium wire, 0.75 g, was dissolved in 300 mL of ammonia at -78° C. A solution of 10.1 g of 11,11-diphenyl-11-methoxyundec-1-ene in 20 mL of THF was added to the lithium solution and the mixture was stirred at reflux for 30 min. To a reaction vessel were added sequentially 5 mL isoprene, 5 mL of methanol, and 10 g of ammonium chloride and the ammonia allowed to evaporate at room temperature. Diethyl ether was added to the mixture and the solution was washed with water and brine (saturated aqueous sodium chloride). The organic layer was dried and concentrated in vacuo to give 9.7 g of 11,11-diphenylundec-1-ene which is characterized by:

후처리

  1. temperatureat reflux for 30 min
  2. customto evaporate at room temperature
  3. additionDiethyl ether was added to the mixture
  4. washthe solution was washed with water and brine (saturated aqueous sodium chloride)
  5. customThe organic layer was dried
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d7ceb933c0c24dbebec2cb94b509ff9e
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387617

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