Acetylene → 1-(4-Fluorophenyl)-1-(4-methoxyphenyl)-2-propyn-1-ol
Reaction equation
[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]=1Participants
Procedure
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% by 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 ammonium chloride (200 mL), saturated aqueous sodium chloride (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.
Workup
- customseparated
- extractionthe aqueous layer was extracted with three portions of diethyl ether (200 mL)
- washwashed with saturated aqueous ammonium chloride (200 mL), saturated aqueous sodium chloride (200 mL), and saturated aqueous sodium bicarbonate (200 mL)
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customevaporated to an amber colored oil
Sources & evidence
- ORD record
- ord-ddc146cd222f4546a13cdb7193bbdee1
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07465415B2
Reaction notes
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