HCID 178509747, compound → HCID 178447775, compound

HRID 1377400Notes

Reaction equation

HRID 1377400 reaction equation
Cl[SiH:2]1[CH2:7][CH2:6][CH:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1>C1COCC1>[C:24]([C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][CH2:15][CH2:14][C@H:11]2[CH2:12][CH2:13][C@H: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)[CH2:9][CH2:10]2)=[CH:19][CH:20]=1)#[N:25]

Participants

3

Reactant 1

HCID 178509747HCID 178509747, compound

Product 1

HCID 178447775HCID 178447775, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 200 ml of THF and 14.0 g of zinc chloride was dropped in 130 ml (0.13 mols) of a THF solution of 1M of 4-pentenylmagnesium bromide to obtain an organozinc reagent. The resultant mixture was added to a solution of 300 ml of THF and 37.4 g (0.1 mol) of 1-chloro-4-(trans-4-(4-(4-cyanophenyl)butyl)cyclohexyl)-1-silacyclohexane. 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 30.9 g (yield: 76%) 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 30.9 g (yield: 76%) of the intended trans isomer product

Sources & evidence

ORD record
ord-458ae91d2da248b0b2174a8a0af89ab0
Source dataset
uspto-grants-1997_09
Patent number
US05665271

Reaction notes

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