Dimethylformamide → 5-[2-(1,3-Dioxolan-2-yl)ethoxy]-2,3-difluoropyridine

HRID 1517278Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:8][CH2:9][CH:10]1[O:14][CH2:13][CH2:12][O:11]1.CN(C)C=O.[F:20][C:21]1[CH:22]=[C:23]([OH:28])[CH:24]=[N:25][C:26]=1[F:27]>O>[O:11]1[CH2:12][CH2:13][O:14][CH:10]1[CH2:9][CH2:8][O:28][C:23]1[CH:22]=[C:21]([F:20])[C:26]([F:27])=[N:25][CH:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Cesium carbonate (33 g, 100 mmol) and 2-(2-bromoethyl)-1,3-dioxolane (12 g, 67 mmol) were added to an N,N-dimethylformamide suspension (30 ml) of 5,6-difluoropyridin-3-ol (8.8 g, 67 mmol), and stirred at 100° C. for 1 hour. The reaction solution was cooled to room temperature, water was added, and extracted with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:chloroform=1:1 to 0:1) to obtain 5-[2-(1,3-dioxolan-2-yl)ethoxy]-2,3-difluoropyridine (5.9 g, yield: 38%) as a pale yellow oil.

Workup

temperatureThe reaction solution was cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated saline water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane:chloroform=1:1 to 0:1)

Sources & evidence

ORD record: ord-d4c0287df12441738b873d1c079941c1
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232284B2

Reaction notes

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