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

HRID 1899440Notes

Reaction equation

[C:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C([Li])(CC)C.CN(C)[CH:27]=[O:28]>O1CCCC1.C(OCC)(=O)C>[F:19][C:14]1[C:13]([C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:18][CH:17]=[CH:16][C:15]=1[CH:27]=[O:28]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 7.00 g (27.0 mmol) of 2-(1-dodecynyl)fluorobenzene in tetrahydrofuran (60 ml) at -78° C. was added slowly sec-butyllithium (1.3M, cyclohexane) (21 ml). The mixture was stirred at -78° C. for 30 rain, and dimethylformamide (2.8 ml) was added dropwise. The mixture was stirred for 5 min at -78° C. and allowed to warm to room temperature. The mixture was diluted with ethyl acetate and washed with water. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated in vacuo. The residue was flash chromatographed on silica gel (eluted with ethyl acetate/heptane/1:10). The appropriate fractions were collected and evaporated. The residue was chromatographed a second time over silica gel (eluted with dichloromethane) to afford 7.10 g (91%) of product.

Workup

additionwas added dropwise
temperatureto warm to room temperature
washwashed with water
customThe organic phase was separated
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationthe filtrate concentrated in vacuo
customchromatographed on silica gel (eluted with ethyl acetate/heptane/1:10)
customThe appropriate fractions were collected
customevaporated
customThe residue was chromatographed a second time over silica gel (eluted with dichloromethane)

Sources & evidence

ORD record: ord-e44a841af9164bd4898ad3002aa1edb3
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05571923

Reaction notes

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