Sodium hydride → 5-(10-Bromodecyloxy)-1,8-nonadiene

HRID 1755611Notes

Reaction equation

HRID 1755611 reaction equation
[H-].[Na+].[CH2:3]=[CH:4][CH2:5][CH2:6][CH:7]([OH:12])[CH2:8][CH2:9][CH:10]=[CH2:11].[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br>C1COCC1>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:12][CH:7]([CH2:8][CH2:9][CH:10]=[CH2:11])[CH2:6][CH2:5][CH:4]=[CH2:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2214831,10-DibromodecaneHCID 118295421,8-Nonadien-5-ol

Product 1

HCID 199176565-(10-Bromodecyloxy)-1,8-nonadieneYield 31.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.1 g of 60% sodium hydride was suspended in 50 ml of THF, and 6.6 g of 1,8-nonadien-5-ol was dropped therein in an atmosphere of argon. 28 g of 1,10-dibromodecane was further dropped therein, and reflux was then carried out for 21 hours in an atmosphere of argon. After the generated precipitate was filtered off, the solvent was evaporated, and the residue was purified by silica gel column chromatography, to obtain 5.3 g of the compound (7). (Yield: 31%)

Workup

  1. temperaturereflux
  2. filtrationAfter the generated precipitate was filtered off
  3. customthe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a89b77f94e864dc4af9e64c9bbaf5f6a
Source dataset
uspto-grants-1995_08
Patent number
US05437816

Reaction notes

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