Pyridine → 1-Vinyl-1-triethylsilanyloxy-cyclopentane

HRID 400219Notes

Reaction equation

HRID 400219 reaction equation
N1C=CC=CC=1.[C:7]([C:9]1([O:14][Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])[CH2:13][CH2:12][CH2:11][CH2:10]1)#[CH:8].[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCCCCC>[CH:7]([C:9]1([O:14][Si:15]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:20][CH3:21])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[CH2:8]

Participants

6

Reactant 3

HCID 1049PyridineHCID 226391411-Ethynyl-1-triethylsiloxycyclopentaneHCID 178418361HCID 178418361, compound

Product 1

HCID 189444931-Vinyl-1-triethylsilanyloxy-cyclopentane

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8058HexaneSolvent2×

Procedure

Lindlar catalyst (250 mg) was prehydrogenated in hexane (40 ml) and pyridine (0.25 ml) for 30 min.; after addition of 1-Ethinyl-1-triethylsilanyloxy-cyclopentane (11.22 g; 50.0 mmole) dissolved in hexane (80 ml) hydrogenation was continued at ambient temperature and normal pressure until the uptake of hydrogen ceased; the catalyst was removed by filtration through a plug of neutral alumina (act. 3); after removal of the solvent under reduced pressure the crude product was purified by distillation. 1-Vinyl-1-triethylsilanyloxy-cyclopentane (B1) was obtained as a colourless oil; bp.: 100° C. (0.2 mbar), Kugelrohr.

Workup

  1. customwas continued at ambient temperature
  2. customthe catalyst was removed by filtration through a plug of neutral alumina (act. 3)
  3. customafter removal of the solvent under reduced pressure the crude product
  4. distillationwas purified by distillation

Sources & evidence

ORD record
ord-6b7f9ff29bc84de2952902d5811c7688
Source dataset
uspto-grants-1998_10
Patent number
US05827883

Reaction notes

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