2-Fluoropyridine → (4-(Pyridin-2-yloxymethyl)-phenyl)-methanol

HRID 1927258Notes

Reaction equation

[C:1]1([CH2:9][OH:10])[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[H-].[Na+]>CN(C=O)C>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[O:8][CH2:7][C:4]1[CH:5]=[CH:6][C:1]([CH2:9][OH:10])=[CH:2][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1,4-benzenedimethanol (5.5 g) and DMF (15 mL) of 2-fluoropyridine (1.3 g) was added NaH (1.4 g/66% in oil) at 0° C., which was stirred for 1 hour at 70° C. The reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1) to obtain the titled compound (1.9 g).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
customthe solvent was evaporated under a reduced pressure
customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:1)

Sources & evidence

ORD record: ord-00603c339d724c3f926a814528ded53b
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183264B2

Reaction notes

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