Triethyl Phosphate → HCID 178447754, compound

HRID 1080577Notes

Reaction equation

HRID 1080577 reaction equation
Br[CH:2]1[CH2:7][CH2:6][SiH:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:4][CH2:3]1.[Mg].P(OCC)(OCC)(OCC)=O.Br[CH2:26][CH2:27][C@H:28]1[CH2:33][CH2:32][C@H:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]3[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=3)=[CH:36][CH:35]=2)[CH2:30][CH2:29]1>[Cu]I.C1COCC1>[CH2:8]([Si@H:5]1[CH2:6][CH2:7][C@H:2]([CH2:26][CH2:27][C@H:28]2[CH2:33][CH2:32][C@H:31]([C:34]3[CH:39]=[CH:38][C:37]([C:40]4[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=4)=[CH:36][CH:35]=3)[CH2:30][CH2:29]2)[CH2:3][CH2:4]1)[CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 6535Triethyl PhosphateHCID 5462224MagnesiumHCID 123524839HCID 123524839, compoundHCID 178505507HCID 178505507, compound

Product 1

HCID 178447754HCID 178447754, compoundYield 67.6%

Reagents, catalysts & solvents 2

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

Procedure

24.9 g (0.1 mol) of 1-bromo-4-n-pentyl-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 36.1 g (0.1 mol) of 4-(trans-4-(2-bromoethyl)cyclohexyl)-4'-fluorobiphenyl. After a conventional after treatment, 4-(trans-4-(2-(trans-4-n-pentyl-4-silacyclohexyl)ethyl)cyclohexyl)-4'-fluorobiphenyl 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 30.5 g (yield 67.6%) of the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-c9c832493d764e1b8f5d97af79445d11
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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