Dimethylformamide → 2-Fluoro-3-(1-undecynyl)benzaldehyde
Reaction equation
[C:1]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[F:18])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[O:19]1CCC[CH2:20]1.C([Li])CCC.CN(C)C=O>C(Cl)Cl>[F:18][C:13]1[C:12]([C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:17][CH:16]=[CH:15][C:14]=1[CH:20]=[O:19]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 2-(1-undecynyl)fluorobenzene (7.00 g) and tetrahydrofuran (70 ml) was added slowly n-butyllithium (1.6M, 17.8 ml) at -78° C. The reaction mixture was stirred at -78° C. for 1.5 hrs. Dimethylformamide (2.28 ml) was added slowly, and the solution was allowed to warm to room temperature over 1 hr, with stirring. Methylene chloride (300 ml) was added, and the solution was washed with 50% hydrochloric acid. The aqueous phase was extracted with methylene chloride. The extracts were combined, dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated. The residue was chromatographed on silica (250 g), eluting with hexane followed by ethyl acetate/hexane (1:4). The appropriate fractions were collected and evaporated to provide 3.53 g (45.2%) of product as an oil.
Workup
- temperatureto warm to room temperature over 1 hr
- stirringwith stirring
- washthe solution was washed with 50% hydrochloric acid
- extractionThe aqueous phase was extracted with methylene chloride
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe filtrate was evaporated
- customThe residue was chromatographed on silica (250 g)
- washeluting with hexane
- customThe appropriate fractions were collected
- customevaporated
Sources & evidence
- ORD record
- ord-8bb0ed3ad4ee465282d7231c68d2f138
- Source dataset
- uspto-grants-1994_11
- Patent number
- US05360811
Reaction notes
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