Iodoethane → HCID 21468090, compound

HRID 1939742Notes

Reaction equation

HRID 1939742 reaction equation
[OH:1][CH:2]([C:8]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]2[C:10](=[C:11]([O:22][CH3:23])[CH:12]=[CH:13][C:14]=2[O:20][CH3:21])[C:9]=1[O:24][CH3:25])[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6].[H-].[Na+].I[CH2:29][CH3:30]>O1CCCC1>[CH2:29]([O:1][CH:2]([C:8]1[CH:17]=[C:16]([O:18][CH3:19])[C:15]2[C:10](=[C:11]([O:22][CH3:23])[CH:12]=[CH:13][C:14]=2[O:20][CH3:21])[C:9]=1[O:24][CH3:25])[CH2:3][CH2:4][CH:5]([CH3:7])[CH3:6])[CH3:30]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 14083905HCID 14083905, compound

Product 1

HCID 21468090HCID 21468090, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

850 mg (2.44 mmole) of 2-(1-hydroxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene and 510 mg (12.2 mmole) of sodium hydride (55% dispersion in oil) were dissolved in 10 ml of dry tetrahydrofuran and 1.9 g (12.2 mmole) of iodo-ethane was added thereto under nitrogen gas and then the mixture was refluxed for 3 hours. After adding 20 ml of ice water, the reaction mixture was extracted twice with dichloromethane, dried over anhydrous magnesium sulfate and filtered through a filter paper. The filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (silica gel 2.5×15 cm) using the solvent condition which increases the amount of ethylacetate so that the n-hexane/ethylacetate ratio can vary from 10:1 to 1:1, to obtain 780 mg of the title compound as a pale yellow oil.

Workup

  1. temperatureunder nitrogen gas and then the mixture was refluxed for 3 hours
  2. extractionthe reaction mixture was extracted twice with dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered through a filter paper
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto obtain a crude product
  7. customThe crude product was purified by silica gel column chromatography (silica gel 2.5×15 cm)
  8. temperatureincreases the amount of ethylacetate so that the n-hexane/ethylacetate ratio

Sources & evidence

ORD record
ord-8e4388634ee34bacb4d4569c58172bab
Source dataset
uspto-grants-1997_12
Patent number
US05696276

Reaction notes

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