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

HRID 1050480Notes

Reaction equation

HRID 1050480 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]>CC1C=CC=CC=1C.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Ru]>[CH: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][CH3:3]

Participants

4

Reactant 1

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

Product 1

HCID 669810261-(5-(Prop-1-enyl)benzo[d][1,3]dioxol-2-yl)ethanoneYield 38.2%

Reagents, catalysts & solvents 2

HCID 5364023Ruthenium-tris-acetylacetonatCatalystHCID 7237O-XyleneSolvent

Procedure

3.4 g of 1-(5-allylbenzo[d][1,3]dioxol-2-yl)ethanone and 68 mg (1 mol %) of ruthenium (III) acetylacetonate in 20 ml of o-xylene were stirred 2 days at 130° C., then cooled to room temperature. After concentration of the solvent in vacuum, the crude product was purified by flash chromatography on silica gel to give 1.3 g (38%) of a colorless oil.

Workup

  1. customAfter concentration of the solvent in vacuum, the crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e95b393b1c104ba3b527c7323cd1628a
Source dataset
uspto-grants-2016_07
Patent number
US09382500B2

Reaction notes

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