HCID 131720655, compound → HCID 15824693, compound

HRID 1290613Notes

Reaction equation

HRID 1290613 reaction equation
[CH:1]1([CH2:10][C:11]#[C:12][CH2:13][CH:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H][H]>N1C=CC=CC=1.[Pd]>[CH:14]1([CH2:13]/[CH:12]=[CH:11]\[CH2:10][CH:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15]1

Participants

5

Reactant 2

HCID 131720655HCID 131720655, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15824693HCID 15824693, compoundYield 112.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

A solution is prepared of 20 g (0.0532 moles) of 1,4-bis-(1-indenyl)-but-2-ine in 200 ml of pyridine. The alkyne is then hydrogenated with hydrogen at 1 atm., in the presence of 1.0 g of Pd on BaSO4 (ALDRICH). After 3 hours the absorption of hydrogen stops. The reddish solution is filtered, diluted with water and extracted with diethyl ether. The extract, after evaporation of the solvent, is purified by chromatography on a silica gel column with petroleum ether as eluant. 17 g of 1,4-bis-(1-indenyl)-Z-but-2-ene are obtained with a yield of 85%.

Workup

  1. customAfter 3 hours the absorption of hydrogen
  2. filtrationThe reddish solution is filtered
  3. additiondiluted with water
  4. extractionextracted with diethyl ether
  5. customThe extract, after evaporation of the solvent
  6. customis purified by chromatography on a silica gel column with petroleum ether as eluant

Sources & evidence

ORD record
ord-5949e2d3214c42eb975bb83992b65e6e
Source dataset
uspto-grants-1998_05
Patent number
US05753578

Reaction notes

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