Triethyl Phosphate → HCID 178447755, compound

HRID 1080585Notes

Reaction equation

HRID 1080585 reaction equation
Br[CH2:2][CH2:3][C@H:4]1[CH2:9][CH2:8][Si@H:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:6][CH2:5]1.[Mg].P(OCC)(OCC)(OCC)=O.Br[CH:28]1[CH2:33][CH2:32][CH: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)=[C:36]([F:47])[CH:35]=2)[CH2:30][CH2:29]1>[Cu]I.C1COCC1>[CH2:10]([Si@H:7]1[CH2:8][CH2:9][C@H:4]([CH2:3][CH2:2][C@H:28]2[CH2:29][CH2:30][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)=[C:36]([F:47])[CH:35]=3)[CH2:32][CH2:33]2)[CH2:5][CH2:6]1)[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 6535Triethyl PhosphateHCID 5462224MagnesiumHCID 23364823HCID 23364823, compoundHCID 178447742HCID 178447742, compound

Product 1

HCID 178447755HCID 178447755, compoundYield 29.2%

Reagents, catalysts & solvents 2

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

Procedure

27.7 g (0.1 mol) of trans-1-(2-bromoethyl)-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 35.1 g (0.1 mol) of 4-(4-bromocyclohexyl)-2,4'-difluorobiphenyl. After a conventional after treatment, 4-(trans-4-(2-(trans-4-n-pentyl-4-silacyclohexyl)ethyl)cyclohexyl)-2,4'-difluorobiphenyl 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 13.1 g (yield 29.2%) of the trans isomer.

Workup

  1. customto obtain a Grignard's reagent

Sources & evidence

ORD record
ord-20d3af8928c54ff1b66d8c917d2a2a4a
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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