Water → 5-(Cyclohexylmethoxy)pentyl bromide

HRID 344246Notes

Reaction equation

HRID 344246 reaction equation
[H-].[Na+].[CH:3]1([CH2:9][OH:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Cl.O>CN(C)C=O>[CH:3]1([CH2:9][O:10][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][Br:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 7507CyclohexanemethanolHCID 24758Sodium hydrideHCID 960701-Bromo-5-chloropentane

Product 1

HCID 540154315-(Cyclohexylmethoxy)pentyl bromideYield 419.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

60% Sodium hydride (1.16 g) was suspended in dimethylformamide (40 ml), and a solution of cyclohexanemethanol (0.3 g) in dimethylformamide (10 ml) was dropwise added under ice-cooling with stirring, which was followed by stirring at room temperature for 1 hr. The mixture was again ice-cooled, and a solution of 1-bromo-5-chloropentane (4.88 g) in dimethylformamide (10 ml) was dropwise added, which was followed by stirring at room temperature for 2.5 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 2.9 g of 5-(cyclohexylmethoxy)pentyl bromide.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 1 hr
  3. temperaturecooled
  4. stirringby stirring at room temperature for 2.5 hr
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed successively with water and brine
  7. customdried
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-a20b8a446870428189fcc03651067d89
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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