Acetylene → 1-(4-Fluorophenyl)-1-(4-methoxyphenyl)-2-propyn-1-ol

HRID 225393

반응식

HRID 225393 반응식
[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH:18]#[CH:19].[C-]#[C-].[Na+].[Na+]>>[F:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)([OH:7])[C:18]#[CH:19])=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 6326AcetyleneHCID 676644-Fluoro-4'-methoxybenzophenoneHCID 178463197HCID 178463197, 화합물

생성물 1

HCID 866027791-(4-Fluorophenyl)-1-(4-methoxyphenyl)-2-propyn-1-ol

실험 절차

4-Fluoro-4′-methoxy-benzophenone from Step 1 (126.7 grams) and acetylene saturated N,N-dimethylformamide (380 mL) were combined in a reaction flask. Sodium acetylide solution (9 weight % in toluene, 343 grams) was added to the reaction mixture dropwise over 45 minutes. The reaction mixture was stirred at room temperature for 1 hour and then poured into ice water (600 mL). The layers were phase separated and the aqueous layer was extracted with three portions of diethyl ether (200 mL). The organic layers were combined and washed with saturated aqueous NH4Cl (200 mL), saturated aqueous NaCl (200 mL), and saturated aqueous sodium bicarbonate (200 mL). The organic layer was dried over anhydrous sodium sulfate and evaporated to an amber colored oil yielding 136.6 grams of 1-(4-fluorophenyl)-1-(4-methoxyphenyl)-2-propyn-1-ol. This material was not purified further but was used directly in the next step.

후처리

  1. customseparated
  2. extractionthe aqueous layer was extracted with three portions of diethyl ether (200 mL)
  3. washwashed with saturated aqueous NH4Cl (200 mL), saturated aqueous NaCl (200 mL), and saturated aqueous sodium bicarbonate (200 mL)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated to an amber colored oil

출처 및 근거

ORD 기록
ord-ba0ce24846e3467bbeefbf4f3f25d544
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07556751B2

연결된 노트

불러오는 중…