4-Bromopent-1-ene → HCID 178447769, compound

HRID 1440360Notes

Reaction equation

HRID 1440360 reaction equation
Br[CH:2]([CH3:6])[CH2:3][CH:4]=[CH2:5].[Mg].Cl[SiH:9]1[CH2:14][CH2:13][CH:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[C:25]([F:30])[CH:24]=3)[CH2:17][CH2:16]2)[CH2:11][CH2:10]1>C1COCC1>[F:30][C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][C@H:18]2[CH2:19][CH2:20][C@H:15]([C@H:12]3[CH2:13][CH2:14][Si@H:9]([CH2:5][CH2:4][CH2:3][CH:2]=[CH2:6])[CH2:10][CH2:11]3)[CH2:16][CH2:17]2)[CH:28]=[CH:27][C:26]=1[F:29]

Participants

5

Reactant 3

HCID 1416754-Bromopent-1-eneHCID 5462224MagnesiumHCID 178505680HCID 178505680, compound

Product 1

HCID 178447769HCID 178447769, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.0 g (20 mmol) of 4-bromopentene 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 6.5 g (yield 83%) of trans-4-(trans-4-(2-(3,4-difluorophenyl) ethyl) cyclohexyl)-1-(4-pentenyl)-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-318654150a174fcb971082812288f7f0
Source dataset
uspto-grants-1996_03
Patent number
US05498737

Reaction notes

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