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

HRID 1638298Notes

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 thyl 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 thyl 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-73949e8ad96649d8877ce53ad9d86397
Source dataset: uspto-grants-1989_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04879292

Reaction notes

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