Triethyl Phosphate → HCID 178460934, compound

HRID 1080578Notes

Reaction equation

HRID 1080578 reaction equation
Br[CH:2]1[CH2:7][CH2:6][SiH:5]([CH2:8][CH2:9][CH3:10])[CH2:4][CH2:3]1.[Mg].P(OCC)(OCC)(OCC)=O.I[CH2:24][CH2:25][C@H:26]1[CH2:31][CH2:30][C@H:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38]3[CH:43]=[CH:42][C:41]([C:44]([F:47])([F:46])[F:45])=[C:40]([F:48])[CH:39]=3)=[CH:34][CH:33]=2)[CH2:28][CH2:27]1>[Cu]I.C1COCC1>[CH2:8]([Si@H:5]1[CH2:6][CH2:7][C@H:2]([CH2:24][CH2:25][C@H:26]2[CH2:27][CH2:28][C@H:29]([C:32]3[CH:37]=[CH:36][C:35]([C:38]4[CH:43]=[CH:42][C:41]([C:44]([F:45])([F:46])[F:47])=[C:40]([F:48])[CH:39]=4)=[CH:34][CH:33]=3)[CH2:30][CH2:31]2)[CH2:3][CH2:4]1)[CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 6535Triethyl PhosphateHCID 5462224MagnesiumHCID 123319161HCID 123319161, compoundHCID 178505436HCID 178505436, compound

Product 1

HCID 178460934HCID 178460934, compoundYield 72.3%

Reagents, catalysts & solvents 2

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

Procedure

22.1 g (0.1 mol) of 1-bromo-4-n-propyl-4-silacyclohexane 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 47.6 g (0.1 mol) of 4-(trans-4-(2-iodoethyl)cyclohexyl)-3'-fluoro-4'-trifluoromethylbiphenyl. After a conventional after treatment, 4-(trans-4-(2-(trans-4-n-propyl-4-silacyclohexyl)ethyl)cyclohexyl)-3'-fluoro-4'-trifluoromethylbiphenyl 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 35.5 g (yield 72.3%) of the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-134dc50bab3d41148310466cce0f7f7b
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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