Dimethylformamide → 2-Fluoro-3-(1-undecynyl)benzaldehyde

HRID 1601175Notes

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 (1.6 M, 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-7d75f6d41c9f4b349d65b2eb0322f185
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977147

Reaction notes

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