Hydrochloric Acid → HCID 59526956, compound

HRID 384472Notes

Reaction equation

HRID 384472 reaction equation
CN(C=[O:5])C.O.[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH2:26])[CH:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>CN(C=O)C.[Pd](Cl)Cl.[Cu]Cl>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[O:21][CH2:22][CH2:23][CH2:24][C:25](=[O:5])[CH3:26])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 21962138N,N-Dimethylformamide--water (1/1)HCID 59527483HCID 59527483, compound

Product 1

HCID 59526956HCID 59526956, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

Palladium(II) chloride (112 mg) and copper(I) chloride (628 mg) were added to DMF-water (7:1, 8 mL), followed by stirring at room temperature under oxygen atmosphere for 1 hour. A solution of 1-(benzyloxy)-3-(pent-4-en-1-yloxy)benzene (1.70 g) in DMF (7 mL) was added dropwise to the reaction mixture, followed by vigorous stirring at room temperature for 2 hours. 0.5M Hydrochloric acid (60 mL) was added to the reaction mixture, followed by extraction with diethyl ether (100 mL). The organic layer was washed sequentially with water and saturated brine, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=5/1) to obtain 5-[3-(benzyloxy)phenoxy]pentan-2-one (1.65 g).

Workup

  1. stirringby vigorous stirring at room temperature for 2 hours
  2. extractionfollowed by extraction with diethyl ether (100 mL)
  3. washThe organic layer was washed sequentially with water and saturated brine
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-4a36ca28b1bc442b937268e42550be8c
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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