1,6-Dibromohexane → 2-[2-[(6-Bromohexyl)oxy]ethyl]-6-methylpyridine

HRID 2108020Notes

Reaction equation

HRID 2108020 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:4][CH:3]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br>C(OCC)(=O)C>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:10][CH2:9][CH2:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 2

HCID 123681,6-DibromohexaneHCID 702836-Methylpyridine-2-ethanol

Product 1

HCID 230450492-[2-[(6-Bromohexyl)oxy]ethyl]-6-methylpyridineYield 82.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

From 6-methyl-2-pyridineethanol (5 g) and 1,6-dibromohexane (26 g), stirring the reaction mixture under nitrogen for 18 h, and using ethyl acetate for extraction. FCC eluting with cyclohexane→cyclohexane-ethyl acetate (92:8) gave the title compound as a yellow oil (9 g), t.l.c. (System A 80:20:1) Rf 0.6.

Workup

  1. extractionfor extraction
  2. washFCC eluting with cyclohexane→cyclohexane-ethyl acetate (92:8)

Sources & evidence

ORD record
ord-bfe72a7401c145ce9e3457386b7853d9
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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