HCID 67669255, compound → HCID 19423901, compound

HRID 743410Notes

Reaction equation

HRID 743410 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20]CC2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.[Pd]>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[OH:20])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 67669255HCID 67669255, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19423901HCID 19423901, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The whole of this benzyl 2-(7-phenyl-1-heptenyl)phenyl ether was then treated with hydrogen in the presence of 200 mg of 5% w/w palladium-on-carbon in 250 ml of ethanol at 50° C. for 5 hours at atmospheric pressure. At the end of this time, insoluble materials were removed by filtration, and the filtrate was concentrated by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 1.03 g (yield 69%) of the title compound as a colorless oil.

Workup

  1. customAt the end of this time, insoluble materials were removed by filtration
  2. concentrationthe filtrate was concentrated by distillation under reduced pressure
  3. customThe resulting residue was purified by column chromatography through silica gel
  4. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-42b5f07346c5480c8fc399f62d0f6723
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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