Diethyl Ether → HCID 524846, compound

HRID 868024Notes

Reaction equation

HRID 868024 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.C([Li])CCC.[CH2:16](I)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(OCC)C>C1COCC1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 90251,3-DimethoxybenzeneHCID 202741-IodoheptaneHCID 178418339Butyllithium

Product 1

HCID 524846HCID 524846, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

1,3-dimethoxybenzene (0.25 mol, 34 ml) was dissolved in THF (1 liter, dried) and the resultant solution was cooled in an ice bath. n-Butyl lithium (200 ml, 0.32 moles) was added over a period of one hour. The resultant solution was stirred for 2 hours in an ice bath. Solution was then cooled to -78° C. and n-heptyl iodide (226 ml, 0.22 moles) was quickly added. The solution was then allowed to warm to room temperature and stirred overnight then refluxed for 2 hours. The solution was cooled and a mixture of diethyl ether and water was added. The ether layer was collected, dried over magnesium sulfate, filtered and evaporated to dryness. The residue was chromatographed by HPLC (eluted with hexane) to yield 34.0 g of the title product.

Workup

  1. temperatureto warm to room temperature
  2. temperaturethen refluxed for 2 hours
  3. temperatureThe solution was cooled
  4. additionwas added
  5. customThe ether layer was collected
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue was chromatographed by HPLC (eluted with hexane)

Sources & evidence

ORD record
ord-d3721f313d3b4cf78a30ef469f48c0cc
Source dataset
uspto-grants-1988_10
Patent number
US04777299

Reaction notes

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