HCID 178460925, compound → HCID 178460915, compound

HRID 1080574Notes

Reaction equation

HRID 1080574 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Mg]Br)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.I[CH:17]1[CH2:22][CH2:21][CH:20]([C@H:23]2[CH2:28][CH2:27][Si@H:26]([CH2:29][CH2:30][CH3:31])[CH2:25][CH2:24]2)[CH2:19][CH2:18]1>[Cu]I.C1COCC1>[CH2:29]([SiH:26]1[CH2:25][CH2:24][CH:23]([C@H:20]2[CH2:21][CH2:22][C@H:17]([C:11]3[CH:12]=[CH:13][C:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)=[CH:9][CH:10]=3)[CH2:18][CH2:19]2)[CH2:28][CH2:27]1)[CH2:30][CH3:31]

Participants

5

Reactant 2

HCID 178460925HCID 178460925, compoundHCID 178505512HCID 178505512, compound

Product 1

HCID 178460915HCID 178460915, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A 15 ml THF solution of 1.5M 4-(4-fluorophenyl)phenyl magnesium bromide (22.5 mmol) was dripped into a mixed solution of 7.0 g (20.0 mmol) of trans-4-(4-iodocyclohexyl)-1-n-propyl-1-silacyclohexane, 70 mg of copper (I) iodide and 50 ml of THF. The silacyclohexane rings of the product thus obtained were a mixture of trans isomers and cis isomers. After a conventional after treatment, they were separated by means of chromatography to obtain 2.29 g (yield 58%) of the target product, i.e. the trans, trans isomers. The obtained target product exhibited the same physical properties as the product of Example 8.

Workup

  1. customThe silacyclohexane rings of the product thus obtained
  2. additiona mixture of trans isomers and cis isomers
  3. customAfter a conventional after treatment, they were separated by means of chromatography

Sources & evidence

ORD record
ord-3cd8ef3a0ba945b7810bbd7f9b2348ba
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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