HCID 178445934, compound → HCID 178447776, compound

HRID 1377401Notes

Reaction equation

HRID 1377401 reaction equation
[CH:1]([Mg]Cl)=[CH:2][CH2:3][CH2:4][CH3:5].Cl[SiH:9]1[CH2:14][CH2:13][CH:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[C:29]([F:31])[C:28]([C:32]#[N:33])=[C:27]([F:34])[CH:26]=3)[CH2:17][CH2:16]2)[CH2:11][CH2:10]1>C1COCC1>[F:34][C:27]1[CH:26]=[C:25]([CH2:24][CH2:23][CH2:22][CH2:21][C@H:18]2[CH2:19][CH2:20][C@H:15]([C@H:12]3[CH2:13][CH2:14][Si@H:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:10][CH2:11]3)[CH2:16][CH2:17]2)[CH:30]=[C:29]([F:31])[C:28]=1[C:32]#[N:33]

Participants

4

Reactant 2

HCID 178445934HCID 178445934, compoundHCID 178510277HCID 178510277, compound

Product 1

HCID 178447776HCID 178447776, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

50 ml (0.13 mols) of a THF solution of 2.5M of pentenylmagnesium chloride was dropped in a mixed solution of 41.0 g (0.1 mol) of 1-chloro-4-(trans-4-(4-(3,5-difluoro-4-cyanophenyl)butyl)cyclohexyl)-1-silacyclohexane and 300 ml of THF. The resultant product was found to be a mixture of trans and cis isomers with respect to the silacyclohexane ring. The product was subjected to ordinary aftertreatments such as removal of solvent and salts, followed by isolation through chromatography to obtain 40.1 g (yield: 90%) of the intended trans isomer product.

Workup

  1. additiona mixture of trans and cis isomers with respect to the silacyclohexane ring
  2. customThe product was subjected to ordinary aftertreatments such as removal of solvent and salts
  3. customto obtain 40.1 g (yield: 90%) of the intended trans isomer product

Sources & evidence

ORD record
ord-53b6b7e3c2304b1884cfc3fb8ee57442
Source dataset
uspto-grants-1997_09
Patent number
US05665271

Reaction notes

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