HCID 178509792, compound → HCID 178447751, compound

HRID 1377407Notes

Reaction equation

HRID 1377407 reaction equation
Cl[SiH:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)[CH2:4][CH2:3]1>C1COCC1>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([C@H:15]2[CH2:16][CH2:17][C@H:12]([CH2:11][CH2:10][CH2:9][CH2:8][C@H:5]3[CH2:6][CH2:7][Si@H:2]([CH2:7][CH2:6][CH2:5][CH:4]=[CH2:3])[CH2:3][CH2:4]3)[CH2:13][CH2:14]2)=[CH:19][CH:20]=1)#[N:25]

Participants

3

Reactant 1

HCID 178509792HCID 178509792, compound

Product 1

HCID 178447751HCID 178447751, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

130 ml (0.13 mols) of a THF solution of 1M of 4-pentenylmagnesium bromide was dropped in a solution of 200 ml of THF and 14.0 g of zinc chloride to obtain an organozinc reagent. The resultant mixture was added to a solution of 41.0 g (0.1 mol) of 1-chloro-4-(4-(trans-4-(4-cyanophenyl)cyclohexyl)butyl)-1-silacyclohexane in 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, followed by isolation through chromatography to obtain 40.8 g (yield: 95%) of the intended trans isomer product.

Workup

  1. additiona mixture of trans and cis isomers with respect to the silacyclohexane ring
  2. customto obtain 40.8 g (yield: 95%) of the intended trans isomer product

Sources & evidence

ORD record
ord-d5cda2641452451bbace764534219d10
Source dataset
uspto-grants-1997_09
Patent number
US05665271

Reaction notes

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