1,10-Phenanthroline → HCID 59527293, compound

HRID 384451Notes

Reaction equation

HRID 384451 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C2C(=CC=C3C=2N=CC=C3)C=[CH:16][CH:15]=1.C(OCC)=C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.ClCCl>[CH:15]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[CH2:16]

Participants

6

Reactant 3

HCID 13181,10-PhenanthrolineHCID 8023Ethyl vinyl etherHCID 5622124-Benzyloxy-1-butanol2×

Product 1

HCID 59527293HCID 59527293, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Under reaction conditions as described in J. Org. Chem. 1997, 62, 1560, {[4-(vinyloxy)butoxy]methyl}benzene was obtained using 4-(benzyloxy)butan-1-ol as a starting material. That is, 1,10-phenanthroline (1.00 g) and palladium(II) acetate (2.50 g) were added to a mixture of ethyl vinyl ether (25 mL) and dichloromethane (15 mL), followed by stirring for 15 minutes, and then 4-(benzyloxy)butan-1-ol (5.00 g) was added thereto, followed by stirring at room temperature for 60 hours. The reaction mixture was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=95/5) to obtain {[4-(vinyloxy)butoxy]methyl}benzene (3.24 g).

Workup

  1. stirringby stirring at room temperature for 60 hours
  2. customThe reaction mixture was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=95/5)

Sources & evidence

ORD record
ord-99c517af141245fa9cb631417af4685b
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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