Hexane → [2-(4-Isopropoxy-butyloxy)-ethyl]-piperonyl-thioether

HRID 2398788Notes

Reaction equation

HRID 2398788 reaction equation
[CH2:1]([S:11][CH2:12][CH2:13][OH:14])[C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1.[H-].[Na+].CCCCCC.Br[CH2:24][CH2:25][CH2:26][CH2:27][O:28][CH:29]([CH3:31])[CH3:30]>COCCOC.CCOCC>[CH:29]([O:28][CH2:27][CH2:26][CH2:25][CH2:24][O:14][CH2:13][CH2:12][S:11][CH2:1][C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH2:6][O:5][C:4]=2[CH:3]=1)([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 8058HexaneHCID 24758Sodium hydrideHCID 214340411-Bromo-4-(propan-2-yloxy)butaneHCID 214340522-Piperonylthioethanol

Product 1

HCID 21434047[2-(4-Isopropoxy-butyloxy)-ethyl]-piperonyl-thioether

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

2.12 g (0.01 mol) of 2-piperonylthioethanol are added at room temperature over the course of 10 minutes, to a suspension of 0.48 g (0.01 mol) of 50% sodium hydride dispersion, which had been freed from the mineral oil with hexane, in 40 cc of 1,2-dimethoxy ethane. The mixture is stirred at 50° for 3 hours and a solution of 1.95 g (0.01 mol) of 1-bromo-4-isopropoxybutane in 30 cc of 1,2-dimethoxy ethane is subsequently added. The mixture is stirred at 60° over the course of 48 hours. After cooling to 20°, 100 cc of ether are added to the reaction mixture. The ether solution is extracted with saturated sodium chloride solution, dried over sodium sulphate and evaporated. The residue is purified by chromatography on silica gel with hexane/ethyl acetate (5:1), whereupon [2-(4-isopropoxy-butyloxy)-ethyl]-piperonylthioether is obtained as a slightly yellow, clear oil.

Workup

  1. stirringThe mixture is stirred at 60° over the course of 48 hours
  2. temperatureAfter cooling to 20°
  3. extractionThe ether solution is extracted with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe residue is purified by chromatography on silica gel with hexane/ethyl acetate (5:1), whereupon [2-(4-isopropoxy-butyloxy)-ethyl]-piperonylthioether
  7. customis obtained as a slightly yellow, clear oil

Sources & evidence

ORD record
ord-6dda5085ecb54457add35843f4d71386
Source dataset
uspto-grants-1977_05
Patent number
US04025641

Reaction notes

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