2-[3-(2-Cyanoethenyl)phenyl]-[1,3]dioxolane → 2-[3-(2-Cyanoethyl)phenyl]-[1,3]dioxolane

HRID 1669354Notes

Reaction equation

HRID 1669354 reaction equation
[C:1]([CH:3]=[CH:4][C:5]1[CH:6]=[C:7]([CH:11]2[O:15][CH2:14][CH2:13][O:12]2)[CH:8]=[CH:9][CH:10]=1)#[N:2]>C(OCC)(=O)C.[C].[Pd]>[C:1]([CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:11]2[O:12][CH2:13][CH2:14][O:15]2)[CH:8]=[CH:9][CH:10]=1)#[N:2]

Participants

4

Reactant 1

HCID 673467182-[3-(2-Cyanoethenyl)phenyl]-[1,3]dioxolane

Product 1

HCID 231317192-[3-(2-Cyanoethyl)phenyl]-[1,3]dioxolane

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4.48 g of a cis-trans isomer mixture of 2-[3-(2-cyanoethenyl)phenyl]-[1,3]dioxolane in 100 ml of ethyl acetate was added 0.60 g of 5% palladium carbon to perform hydrogenation. The catalyst was filtered by filtration with Celite, and the filtrate was concentrated under reduced pressure to obtain 3.52 g of 2-[3-(2-cyanoethyl)phenyl]-[1,3]dioxolane.

Workup

  1. filtrationThe catalyst was filtered by filtration with Celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b20d9b753a7043b1be5c173bc25f2207
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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