Hepta-1,6-dien-4-ol → HCID 11078067, compound

HRID 1755608Notes

Reaction equation

HRID 1755608 reaction equation
[H-].[Na+].[CH2:3]=[CH:4][CH2:5][CH:6]([OH:10])[CH2:7][CH:8]=[CH2:9].[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br>C1COCC1>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:10][CH:6]([CH2:7][CH:8]=[CH2:9])[CH2:5][CH:4]=[CH2:3]

Participants

5

Reactant 3

HCID 17902Hepta-1,6-dien-4-olHCID 24758Sodium hydrideHCID 2214831,10-Dibromodecane

Product 1

HCID 11078067HCID 11078067, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

8.9 g of 60% sodium hydride was suspended in 100 ml of THF, and 25 g of 1,6-heptadien-4-ol dissolved in 50 ml of THF was dropped therein in an atmosphere of argon. 94 g of 1,10-dibromodecane dissolved in 50 ml of THF was further dropped therein, and reflux was carried out for 13 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 19 g of the compound (4). (Yield: 26%)

Workup

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

Sources & evidence

ORD record
ord-5c91cf54109848958ee358a4e033bb73
Source dataset
uspto-grants-1995_08
Patent number
US05437816

Reaction notes

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