HCID 123545774, compound → HCID 178448135, compound

HRID 2209367Notes

Reaction equation

HRID 2209367 reaction equation
Cl[SiH:2]1[CH2:7][CH2:6][CH:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1>C1COCC1>[CH2:5]([C@H:8]1[CH2:15][CH2:14][C@H:11]([SiH:2]2[CH2:7][CH2:6][CH:5]([C:8]3[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=3)[CH2:4][CH2:3]2)[CH2:10][CH2:9]1)[CH2:4][CH3:3]

Participants

3

Reactant 1

HCID 123545774HCID 123545774, compound

Product 1

HCID 178448135HCID 178448135, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.1 g (20 mmol) of 4-n-propylcyclohexyl bromide was dropped into a mixture of 0.5 g of magnesium (21 mmol) and 50 ml of THF to obtain Grignard reagent. This solution was then added to a mixture of 3.0 g (22 mmol) of zinc chloride and 10 ml of THF to obtain the organozinc reagent. This reagent was then dropped into a 50 ml THF solution of 4.7 g (20 mmol) of 4-(4-chloro-4-silacyclohexyl) benzonitrile to obtain 4-(4-(trans-4-n-propylcyclohexyl)-4-silacyclohexyl) benzonitrile. The silacyclohexane rings of this product were a mixture of trans and cis isomers. They were separated by means of chromatography to obtain 5.4 g of the trans isomer (yield 83%).

Sources & evidence

ORD record
ord-5b6b50f7757845f0b2e2ecf61ecaef3e
Source dataset
uspto-grants-1995_10
Patent number
US05454977

Reaction notes

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