Tetrahydrofuran → HCID 178460948, compound

HRID 1440356Notes

Reaction equation

HRID 1440356 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1.[Mg].[CH2:14]([SiH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:15][CH3:16].[CH2:23]1[CH2:27]O[CH2:25][CH2:24]1>[Cu](Cl)Cl>[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:25][CH2:24][C@H:23]2[CH2:27][CH2:6][C@H:5]([C@H:20]3[CH2:21][CH2:22][Si@H:17]([CH2:14][CH2:15][CH3:16])[CH2:18][CH2:19]3)[CH2:4][CH2:9]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 5210081-Bromo-4-(trifluoromethoxy)benzeneHCID 5462224MagnesiumHCID 123380241HCID 123380241, compound

Product 1

HCID 178460948HCID 178460948, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 24014Cupric ChlorideCatalyst2×

Procedure

4.8 g (20 mmol) of p-trifluoromethoxybromobenzene 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 10 mg of copper chloride (I), 10 mg of copper chloride (II) and 7.3 g (20 mmol) of trans-4-(2-bromoethyl) cyclohexyl)-1-n-propyl-1-silacyclohexane. After a conventional after treatment, 6.6 g (yield 80%) of trans-4-(trans-4-(2-(4-trifluoromethoxyphenyl) ethyl) cyclohexyl)-1-n-propyl-1-silacyclohexane was obtained.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-fc810f6d86d34c06a1e984515dfca1ea
Source dataset
uspto-grants-1996_03
Patent number
US05498737

Reaction notes

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