1-Bromopropane → HCID 178447768, compound

HRID 1440359Notes

Reaction equation

HRID 1440359 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])=[CH:23][CH:22]=3)[CH2:15][CH2:14]2)[CH2:9][CH2:8]1.[CH2:28]1COC[CH2:29]1>>[F:27][C:24]1[CH:25]=[CH:26][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][CH2:3][CH2:28][CH3:29])[CH2:8][CH2:9]3)[CH2:14][CH2:15]2)=[CH:22][CH:23]=1

Participants

5

Reactant 4

HCID 78401-BromopropaneHCID 8028Tetrahydrofuran2×HCID 5462224MagnesiumHCID 178505679HCID 178505679, compound

Product 1

HCID 178447768HCID 178447768, compoundYield 85%

Procedure

3.1 g (20 mmol) of n-propyl 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 6.8 g (20 mmol) of 1-chloro-4-(trans-4-(2-(4-fluorophenyl) 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 6.4 g (yield 85%) of trans-4-(trans-4-(2-(4-fluorophenyl) ethyl) cyclohexyl)-1-n-pentyl-1-silacyclohexane.

Workup

  1. customto obtain a Grignard's reagent
  2. customThe silacyclohexane rings of the reacted mixture 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-eddb7f7c292d455d9a5ebd6fa41f8523
Source dataset
uspto-grants-1996_03
Patent number
US05498737

Reaction notes

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