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

HRID 225393

反応式

HRID 225393 の反応式
[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

参加物

4

反応物 3

HCID 6326AcetyleneHCID 676644-Fluoro-4'-methoxybenzophenoneHCID 178463197HCID 178463197、化合物

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ba0ce24846e3467bbeefbf4f3f25d544
出典データセット
uspto-grants-2009_07
特許番号
US07556751B2

関連ノート

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