1-Pentene → 1-(5-(Hex-2-enyl)benzo[d][1,3]dioxol-2-yl)ethanone

HRID 1050481Notes

Reaction equation

HRID 1050481 reaction equation
[CH2:1]([C:4]1[CH:15]=[CH:14][C:7]2[O:8][CH:9]([C:11](=[O:13])[CH3:12])[O:10][C:6]=2[CH:5]=1)[CH:2]=[CH2:3].[CH2:16]=[CH:17][CH2:18]CC>ClCCl.[Ru](Cl)Cl.C1(C(P(C2CCCCC2)(C2CCCCC2)C2CCCCC2)P(C2CCCCC2)(C2CCCCC2)C2CCCCC2)C=CC=CC=1>[CH2:1]([C:4]1[CH:15]=[CH:14][C:7]2[O:8][CH:9]([C:11](=[O:13])[CH3:12])[O:10][C:6]=2[CH:5]=1)[CH:2]=[CH:3][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 80041-Pentene2×HCID 669811291-(5-Allylbenzo[d][1,3]dioxol-2-yl)ethanone

Product 1

HCID 669810221-(5-(Hex-2-enyl)benzo[d][1,3]dioxol-2-yl)ethanoneYield 19%

Reagents, catalysts & solvents 2

HCID 90332616Dichlororuthenium;tricyclohexyl-[phenyl-(tricyclohexyl-lambda5-phosphanyl)methyl]-lambda5-phosphaneCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(5-allylbenzo[d][1,3]dioxol-2-yl)ethanone (5 g), phenylmethylenebis(tricyclohexylphosphine) ruthenium dichloride (0.9 g) and pent-1-ene (5 g) in dichloromethane (40 ml) was stirred at room temperature. After 2 hours, a control by gc analysis shows 60% conversion, but three additional portions of 5 g of pent-1-ene were added during the reaction time (48 hours) to go to completion. Then, the reaction mixture was filtered on a short column of silica gel and concentrated in vacuum to remove the solvent. Finely the crude product was purified by flash chromatography on silica gel (eluant heptane/ethyl acetate 95/5) to give 0.8 g (19%) of a colorless oil, identified as a 85/15 E/Z mixture.

Workup

  1. additionwere added during the reaction time (48 hours)
  2. filtrationThen, the reaction mixture was filtered on a short column of silica gel
  3. concentrationconcentrated in vacuum
  4. customto remove the solvent
  5. customFinely the crude product was purified by flash chromatography on silica gel (eluant heptane/ethyl acetate 95/5)

Sources & evidence

ORD record
ord-f4e4edc2a8ff414d9fa0596f2aa3d93f
Source dataset
uspto-grants-2016_07
Patent number
US09382500B2

Reaction notes

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