2-Norbornene → HCID 16043477, compound

HRID 259874Notes

Reaction equation

HRID 259874 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[CH:2]2.[Cl:8][SiH:9]([Cl:11])[Cl:10]>C1(C)C=CC=CC=1.[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+]>[Cl:8][Si:9]([Cl:11])([Cl:10])[C@H:2]1[CH2:3][C@H:4]2[CH2:7][C@@H:1]1[CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 103522-NorborneneHCID 24811Trichlorosilane

Product 1

HCID 16043477HCID 16043477, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 61538Palladium, di-mu-chlorobis(eta3-2-propenyl)di-CatalystHCID 1140TolueneSolvent

Procedure

(R)-2-Methoxy-2'-di(4-chlorophenyl)phosphino-1,1'-binaphthyl prepared in Example 3 (7.93 mg, 14.78 mmol) and allylpalladium chloride dimer (1.35 mg, 3.69 μmol=7.38 μmol of palladium) were dissolved in toluene (6.95 g). In the solution, norbornene (6.95 g, 73.81 mmol) was added. After adding trichlorosilane (12.00 g, 88.59 mmol) at 0° C., the mixture was warmed to room temperature, followed by stirring at room temperature for 12 hours. Thereafter, from the reaction mixture, the solvent was evaporated off at 100° C. under reduced pressure of 1 Torr to obtain (1S, 2S, 4R)-2-trichlorosilylnorbornane (16.41 g). Isolation yield, 97%.

Workup

  1. customThereafter, from the reaction mixture, the solvent was evaporated off at 100° C. under reduced pressure of 1 Torr

Sources & evidence

ORD record
ord-e488d0c4d1d944229b4aecd0c6763cd5
Source dataset
uspto-grants-1996_06
Patent number
US05523437

Reaction notes

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