HCID 178505680, compound → HCID 178447770, compound

HRID 1440362Notes

Reaction equation

HRID 1440362 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][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=3)[CH2:10][CH2:9]2)[CH2:4][CH2:3]1>C1COCC1>[F:23][C:18]1[CH:17]=[C: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]([CH2:3][CH2:4][CH:5]([CH3:8])[CH3:6])[CH2:3][CH2:4]3)[CH2:9][CH2:10]2)[CH:21]=[CH:20][C:19]=1[F:22]

Participants

3

Reactant 1

HCID 178505680HCID 178505680, compound

Product 1

HCID 178447770HCID 178447770, compoundYield 176.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.0 g (20 mmol) of 3-methylbutyl bromide was dripped into a mixture of 0. 5 g (21 mmol) of magnesium and 50 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 50 ml THF solution of 7.1 g of 1-chloro-4-(trans-4-(2-(3,4-difluorophenyl) ethyl) cyclohexyl)-1-silacyclohexane. The silacyclohexane rings of the reacted mixture 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 6.9 g (yield 88%) of trans-4-(trans-4-(2-(3,4-difluorophenyl) ethyl) cyclohexyl)-1-(3-methylbutyl)-1-silacyclohexane.

Workup

  1. customThe silacyclohexane rings of the reacted mixture 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-19ea0c8faf0e4ab7bbeaf298e7be0710
Source dataset
uspto-grants-1996_03
Patent number
US05498737

Reaction notes

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