Sodium hydride → HCID 20211968, compound

HRID 1906666Notes

Reaction equation

HRID 1906666 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][OH:15])=[CH:9][CH:8]=1)[CH:4]=[CH2:5].[CH:16]1([CH2:19]Br)[CH2:18][CH2:17]1>CS(C)=O>[CH2:3]([O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][O:15][CH2:19][CH:16]2[CH2:18][CH2:17]2)=[CH:9][CH:8]=1)[CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 10921078HCID 10921078, compound

Product 1

HCID 20211968HCID 20211968, compoundYield 38.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a flask charged with redistilled dimethylsulphoxide (50 ml) and sodium hydride (50% dispersion, 4.8 g) was slowly added 2-(4-allyloxyphenyl)ethanol (17.8 g) at ice-bath temperature. Cyclopropylmethyl bromide (13.5 g) in dry dimethyl sulphoxide (20 ml) was added with cooling under nitrogen. The reaction mixture was stirred at room temperature overnight, poured on to ice-water and extracted into diethyl ether. The organic layer was thoroughly washed with saturated brine, evaporated under reduced pressure and chromatographed on silica using petroleum ether (40°-60°) as an eluant to afford 1-allyloxy-4-[2-(cyclopropylmethoxy)ethyl]benzene (9 g).

Workup

  1. temperaturewith cooling under nitrogen
  2. extractionextracted into diethyl ether
  3. washThe organic layer was thoroughly washed with saturated brine
  4. customevaporated under reduced pressure
  5. customchromatographed on silica
  6. custompetroleum ether (40°-60°)

Sources & evidence

ORD record
ord-083203e0ce08415cbd40b92264ac7afb
Source dataset
uspto-grants-1987_03
Patent number
US04652563

Reaction notes

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