1-Bromopropane → HCID 178460947, compound

HRID 1440354Notes

Reaction equation

HRID 1440354 reaction equation
[CH3:1][CH2:2][CH2:3]Br.[Mg].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][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=3)[CH2:15][CH2:14]2)[CH2:9][CH2:8]1>O1CCCC1>[F:28][C:23]1[CH:22]=[C: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:26]=[CH:25][C:24]=1[F:27]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 5462224MagnesiumHCID 178505680HCID 178505680, compound

Product 1

HCID 178460947HCID 178460947, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2.5 g (20 mmol) of n-propyl bromide was dripped into a mixture of 0.5 g (21 mmol) of magnesium and 50 ml of tetrahydrofuran (hereafter referred to as "THF") to obtain a Grignard's reagent. This solution was then dripped into a 50 ml THF solution of 7.4 g of 1-chloro-4-(trans-4-(2-(3,4-difluorophenyl) ethyl) cyclohexyl)-1-silacyclohexane. The silacyclohexane rings of the product 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 5.8 g (yield 80%) of trans-4-(trans-4-(2-(3,4-difluorophenyl) ethyl) cyclohexyl)-1-n-propyl-1-silacyclohexane.

Workup

  1. customto obtain a Grignard's reagent
  2. customThe silacyclohexane rings of the product thus obtained
  3. additiona mixture of trans isomers and cis isomers
  4. customAfter a conventional after treatment, they were separated by means of chromatography

Sources & evidence

ORD record
ord-2f746980f0e5473585800ac67014eed7
Source dataset
uspto-grants-1996_03
Patent number
US05498737

Reaction notes

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