Pyridine → HCID 68120428, compound

HRID 2398785Notes

Reaction equation

HRID 2398785 reaction equation
[H-].[Na+].[CH2:3]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[CH2:4][CH:5]([CH3:7])[CH3:6].[CH2:21](Br)[C:22]1[CH:30]=[CH:29][C:28]2[O:27][CH2:26][O:25][C:24]=2[CH:23]=1.S(=O)(=O)(O)O.N1C=CC=CC=1>COCCOC.CCOCC>[CH2:3]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][C:22]1[CH:30]=[CH:29][C:28]2[O:27][CH2:26][O:25][C:24]=2[CH:23]=1)[CH2:4][CH:5]([CH3:6])[CH3:7]

Participants

8

Reactant 5

HCID 1049PyridineHCID 1118Sulfuric AcidHCID 24758Sodium hydrideHCID 64514231,3-Benzodioxole, 5-(bromomethyl)-HCID 214340426-(4-Isopentyloxybutyloxy)-hexanol

Product 1

HCID 68120428HCID 68120428, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

0.60 g (0.020 mol) of 80% sodium hydride dispersion are added by portions, at 20°, under nitrogen and while stirring, to 4.02 g (0.0155 mol) of 6-(4-Isopentyloxy-butyloxy)-hexanol in 60 cc of absolute 1,2-dimethoxy-ethane. The mixture is stirred at 60° over the course of 2 hours, cooled to 0° and a solution of 3.65 g (0.017 mol) of piperonyl bromide in 40 cc of absolute 1,2-dimethoxy ethane is added dropwise over the course of 10 minutes. The mixture is stirred at 20° for 3 hours and then at 40° for 20 hours, neutralized with 6N sulphuric acid and together with 1.35 g (0.017 mol) of pyridine heated to 60° over the course of 2 further hours. The reaction product is taken up in ether, washed with water, 6N sulphuric acid, water and saturated sodium chloride solution, dried over magnesium sulphate and evaporated. After chromatography of the residue on silica gel with hexane/acetone (98:2) and (96:4), [6-(4-Isopentyloxybutyloxy)-hexyl]-piperonyl ether is obtained as a colourless oil.

Workup

  1. temperaturecooled to 0°
  2. stirringThe mixture is stirred at 20° for 3 hours
  3. waitat 40° for 20 hours
  4. temperatureheated to 60° over the course of 2 further hours
  5. washwashed with water, 6N sulphuric acid, water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-a44f262f38f94654937fbcb8088e6f93
Source dataset
uspto-grants-1977_05
Patent number
US04025641

Reaction notes

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