Sodium hydride → HCID 19917651, compound

HRID 1755605Notes

Reaction equation

HRID 1755605 reaction equation
[CH2:1]=[CH:2][CH:3]([OH:7])[CH2:4][CH:5]=[CH2:6].[H-].[Na+].[H][H].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]Br>O1CCCC1>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:7][CH:3]([CH2:4][CH:5]=[CH2:6])[CH:2]=[CH2:1]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 791221,5-Hexadien-3-olHCID 2214831,10-DibromodecaneHCID 178418361HCID 178418361, compound

Product 1

HCID 19917651HCID 19917651, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10 g of 1,5-hexadien-3-ol was dissolved in 100 ml of tetrahydrofuran (THF), and the atmosphere was replaced with argon. 4.1 g of 60% sodium hydride was added little by little. After hydrogen gas had ceased to generate, a THF solution of 75 g of 1,10-dibromodecane was added, and reflux was carried out for 8 hours. The insoluble matter generated was filtered off, and the solvent was evaporated. The residue was purified by column chromatography, to obtain 11.3 g of the objective compound (1). (Yield: 35%).

Workup

  1. temperaturereflux
  2. filtrationThe insoluble matter generated was filtered off
  3. customthe solvent was evaporated
  4. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5d8b5db9cb2440608eab08faa8463c29
Source dataset
uspto-grants-1995_08
Patent number
US05437816

Reaction notes

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