Triethyl Phosphate → HCID 178460935, compound

HRID 1080579Notes

Reaction equation

HRID 1080579 reaction equation
Br[CH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.[Mg].P(OCC)(OCC)(OCC)=O.Br[CH:36]1[CH2:41][CH2:40][SiH:39]([CH2:42][CH2:43][CH3:44])[CH2:38][CH2:37]1>[Cu]I.C1COCC1>[CH2:42]([Si@H:39]1[CH2:40][CH2:41][C@H:36]([CH2:2][CH2:3][C@H:4]2[CH2:9][CH2:8][C@H:7]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=4)=[CH:12][CH:11]=3)[CH2:6][CH2:5]2)[CH2:37][CH2:38]1)[CH2:43][CH3:44]

Participants

7

Reactant 4

HCID 6535Triethyl PhosphateHCID 5462224MagnesiumHCID 123319161HCID 123319161, compoundHCID 178477942HCID 178477942, compound

Product 1

HCID 178460935HCID 178460935, compoundYield 22.8%

Reagents, catalysts & solvents 2

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

Procedure

37.8 g (0.1 mol) of 4-(trans-4-(2-bromoethyl)cyclohexyl)-4'-chlorobiphenyl 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 22.1 g (0.1 mol) of 1-bromo-4-n-propyl-4-silacyclohexane. After a conventional after treatment, 4-(trans-4-(2-(trans-4-n-propyl-4-silacyclohexyl)ethyl)cyclohexyl)-4'-chlorobiphenyl 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 10.0 g (yield 22.8%) of the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-e021662cd5714fbaa88fb3e97f94ec53
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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