2-(3,4-Dihydro-2H-4-chromenylidene)acetonitrile → 2-(Chroman-4-yl)acetonitrile

HRID 394667

Reaction equation

HRID 394667 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[CH:11][C:12]#[N:13])[CH2:3][CH2:2]1>C(O)C.[Pd]>[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH2:11][C:12]#[N:13])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 569848342-(3,4-Dihydro-2H-4-chromenylidene)acetonitrile

Product 1

HCID 133627812-(Chroman-4-yl)acetonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The unsaturated compound obtained in Step A (Z+E mixture), solubilised in ethanol (20 ml), is introduced into the reactor of a Parr apparatus. 10% (by weight) palladium-on-carbon is then added. The double bond is hydrogenated at a pressure of 45 psi for 12 hours. The catalyst is removed by filtration; the solvent is then evaporated. The residual oil is purified on a silica column eluted by a mixture of AcOEt/PE 3/7. Colourless oil.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent is then evaporated
  3. customThe residual oil is purified on a silica column
  4. washeluted by a mixture of AcOEt/PE 3/7

Sources & evidence

ORD record
ord-5e8b3bae9636410ab4676fbaad6cae90
Source dataset
uspto-grants-2003_08
Patent number
US06602903B2

Linked notes

Loading…