2-Methylpyridine → 2-[7-(2-Chloro-4-methoxyphenoxy)heptyl]pyridine

HRID 2210520Notes

Reaction equation

HRID 2210520 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH3:7].C([Li])CCC.[Cl:13][C:14]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]SC1SCC(=O)N=1>O1CCCC1>[Cl:13][C:14]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

5

Reactant 3

HCID 79752-MethylpyridineHCID 189218352-{[6-(2-Chloro-4-methoxyphenoxy)hexyl]thio}-4,5-dihydrothiazol-4-oneHCID 178418339Butyllithium

Product 1

HCID 189218682-[7-(2-Chloro-4-methoxyphenoxy)heptyl]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere, add 152 mg. 2-picoline and 1.5 ml. tetrahydrofuran (THF) and cool to -28° C. Add 104 mg. n-butyl lithium and stir about 30 minutes at -78° C. Add 20 mg. of the iodide prepared in Examples 2 and 3 in 1 ml. THF. Stir 1 hour at -78° C., let warm to room temperature and stir about 15 hours. Work up with water and methylene chloride then wash with water and brine then dry over sodium sulfate. Elute on a coarse silica column with methylene chloride then 50% ethylacetate/methylene chloride to obtain the title compound. Prepare the hydrochloride salt by reaction of the title compound with 0.1N HCl.

Workup

  1. additionUnder a nitrogen atmosphere, add 152 mg
  2. additionAdd 104 mg
  3. additionAdd 20 mg
  4. temperaturelet warm to room temperature
  5. stirringstir about 15 hours
  6. washWork up with water and methylene chloride then wash with water and brine
  7. dry with materialthen dry over sodium sulfate
  8. washElute on a coarse silica column with methylene chloride

Sources & evidence

ORD record
ord-5a9572f833da4dbbaffe130053375c2f
Source dataset
uspto-grants-1995_10
Patent number
US05459144

Reaction notes

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