HCID 178455855, compound → HCID 178460951, compound

HRID 1377398Notes

Reaction equation

HRID 1377398 reaction equation
[CH2:1]([Mg]Cl)[CH2:2][CH3:3].Cl[SiH:7]1[CH2:12][CH2:11][CH:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[CH2:15][CH2:14]2)[CH2:9][CH2:8]1>O1CCCC1>[C:29]([C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:21][CH2:20][CH2:19][C@H:16]2[CH2:17][CH2:18][C@H:13]([C@H:10]3[CH2:11][CH2:12][Si@H:7]([CH2:1][CH2:2][CH3:3])[CH2:8][CH2:9]3)[CH2:14][CH2:15]2)=[CH:24][CH:25]=1)#[N:30]

Participants

4

Reactant 2

HCID 178455855HCID 178455855, compoundHCID 178509747HCID 178509747, compound

Product 1

HCID 178460951HCID 178460951, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

50 ml (0.18 moles) of a tetrahydrofuran (hereinafter referred to simply as THF) solution of 2.5M of propylmagnesium chloride was dropped in a mixed solution of 37.4 g (0.1 mol) of 1-chloro-4-(trans-4-(4-(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 the solvent and salts, followed by isolation through chromatography to obtain 30.2 g (yield: 79%) 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 the solvent and salts
  3. customto obtain 30.2 g (yield: 79%) of the intended trans isomer product

Sources & evidence

ORD record
ord-8effb9ae6e8c4b148e8b999ba3cc5216
Source dataset
uspto-grants-1997_09
Patent number
US05665271

Reaction notes

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