Bromide ion → HCID 23021535, compound

HRID 501790Notes

Reaction equation

HRID 501790 reaction equation
[Br-].[CH2:2]([Li])[CH2:3][CH2:4][CH3:5].[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[CH2:24](OCC)C>CCCCCC.C(Cl)Cl>[CH2:7]([O:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:17]([CH:18]=[C:2]2[CH2:24][CH2:5][CH2:4][CH2:3]2)[CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

8

Reactant 5

HCID 259Bromide ionHCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 743423-BenzyloxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 23021535HCID 23021535, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
5 °C

Procedure

5.66 g of cyclopentyltriphenylphosphonim bromide was suspended in 25 mL of diethyl ether, to which 8.8 mL of a solution of n-butyllithium in n-hexane (1.56 M) was added dropwise at −30° C. After the reaction mixture was stirred for one hour at 5° C., 2.67 g of 3-(benzyloxy)benzaldehyde dissolved in 5 mL of diethyl ether was added to the reaction mixture, which was then stirred another one hour at room temperature. The reaction mixture was added to a mixture of methylene chloride and dilute hydrochloric acid, and then the organic phase was separated therefrom. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1] to yield 1.06 g of 1-(benzyloxy)-3-(cyclopentylidenemethyl)benzene as light yellow solid.

Workup

  1. additionwas added dropwise at −30° C
  2. additionwas added to the reaction mixture, which
  3. stirringwas then stirred another one hour at room temperature
  4. customthe organic phase was separated
  5. washAfter the resultant organic phase was washed with water
  6. dry with materiala saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled out under reduced pressure
  8. customThe resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=5:1]

Sources & evidence

ORD record
ord-be04834c72cf46178666ddacabddd357
Source dataset
uspto-grants-2010_08
Patent number
US07772285B2

Reaction notes

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