Triethyl Phosphate → HCID 19602027, compound

HRID 1080586Notes

Reaction equation

HRID 1080586 reaction equation
BrCC[C@H]1CC[C@H](CCCCC)CC1.[Mg].P(OCC)(OCC)(OCC)=O.Cl[SiH]1CCC([C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:45]=[C:44]([F:46])[C:43]([O:47][C:48]([F:51])([F:50])[F:49])=[C:42]([F:52])[CH:41]=3)=[CH:36][CH:35]=2)CC1>[Cu]I.C1COCC1>[F:46][C:44]1[CH:45]=[C:40]([C:37]2[CH:36]=[CH:35][CH:34]=[CH:39][CH:38]=2)[CH:41]=[C:42]([F:52])[C:43]=1[O:47][C:48]([F:49])([F:50])[F:51]

Participants

7

Reactant 4

HCID 6535Triethyl PhosphateHCID 5462224MagnesiumHCID 123407593HCID 123407593, compoundHCID 178444391HCID 178444391, compound

Product 1

HCID 19602027HCID 19602027, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

26.1 g (0.1 mol) of trans-1-(2-bromoethyl)-4-n-pentylcyclohexane was dripped into a mixture of 2.5 g (0.11 mol) of magnesium and 300 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 500 ml THF solution of 0.5 g of triethyl phosphate, 0.1 g of copper (I) iodide and 40.7 g (0.1 mol) of 4-(4-chloro-4-silacyclohexyl)3',5'-difluoro-4'-trifluoromethoxybiphenyl. After a conventional after treatment, 4-(2-(trans-4-n-pentylcyclohexyl)ethyl)-4-silacyclohexyl)-3',5'-difluoro-4'-trifluoromethoxybiphenyl was obtained. The silacyclohexane rings of the product were a mixture of trans isomers and cis isomers. They were separated by means of chromatography to obtain 44.3 g (yield 90.1%) of the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-dbcfa363f8db4edc9ff73b6ccce0c2d3
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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