Tetrahydrofuran → HCID 178447771, compound

HRID 1440357Notes

Reaction equation

HRID 1440357 reaction equation
[CH2:1]([SiH:6]1[CH2:11][CH2:10][CH:9](Br)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[Mg].[F:14][CH:15]1[C:20]([F:24])(OCC)[CH:19]=[CH:18][C:17]([CH:25]2[CH2:30][CH2:29][CH:28](Br)[CH2:27][CH2:26]2)=[CH:16]1.[CH2:32]1COC[CH2:33]1>>[F:14][C:15]1[CH:16]=[C:17]([CH2:25][CH2:30][C@H:29]2[CH2:28][CH2:27][C@H:26]([C@H:9]3[CH2:10][CH2:11][Si@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:7][CH2:8]3)[CH2:33][CH2:32]2)[CH:18]=[CH:19][C:20]=1[F:24]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 5462224MagnesiumHCID 67585376HCID 67585376, compoundHCID 123524839HCID 123524839, compound

Product 1

HCID 178447771HCID 178447771, compoundYield 80%

Procedure

5.0 g (20 mmol) of 1-n-pentyl-4-bromo-1-silacyclohexane 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 6.1 g (20 mmol) of 4-(3,4-difluorophenetyl)-1-bromocyclohexane. The products obtained were separated by means of chromatography to obtain 6.5 g (yield 80%) of trans-4-(trans-4-(2-(3,4-difluorophenyl) ethyl) cyclohexyl)-1-n-pentyl-1-silacyclohexane.

Workup

  1. customto obtain a Grignard's reagent
  2. customThe products obtained
  3. customwere separated by means of chromatography

Sources & evidence

ORD record
ord-d54343358edf4e0487326e21d938447f
Source dataset
uspto-grants-1996_03
Patent number
US05498737

Reaction notes

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