2-Methylpyridine → 2-[3-(4-Phenoxyphenoxy)propyl]pyridine

HRID 579944Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].C([Li])CCC.[O:13]([C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26]Br)=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O1CCCC1>[O:13]([C:20]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][CH2:26][CH2:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:28][CH:29]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: -50 °C

Procedure

To a solution of α-picoline (1.0 g, 11 mmol) in dry tetrahydrofuran (20 ml), n-butyl lithium (8 ml, 11 mmol; 1.4 mmol/ml) was added at -50° C. under nitrogen stream until the reaction mixture turned red. After stirring at -50° C. for 30 minutes, 2-(4-phenoxyphenoxy)ethyl bromide (3.0 g, 10 mmol) was dropwise added thereto at -50° C., and stirring was continued at the same temperature for 2 hours and at 20° C. for 12 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography to give 2-[3-(4-phenoxyphenoxy)propyl]pyridine (1.6 g) as pale yellow oil. nD24.5 1.5861.

Workup

stirringat -50° C., and stirring
waitwas continued at the same temperature for 2 hours and at 20° C. for 12 hours
extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with an aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
customAfter removal of the solvent
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-cad3c7cf578348aa991e3141700c8d7c
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04751225

Reaction notes

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