Triethyl Phosphate → HCID 131720184, compound

HRID 1377410Notes

Reaction equation

HRID 1377410 reaction equation
P(OCC)(OCC)(OCC)=O.BrCCCC[C@H:17]1[CH2:22][CH2:21][Si@H:20]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:18]1>C1COCC1.[Cu]I>[CH2:23]([SiH:20]1[CH2:21][CH2:22][CH2:17][CH2:18][CH2:19]1)[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 2

HCID 6535Triethyl PhosphateHCID 178455405HCID 178455405, compound

Product 1

HCID 131720184HCID 131720184, compoundYield 37%

Reagents, catalysts & solvents 2

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

Procedure

33.5 g (0.1 mol) of 4-(4-bromocyclohexyl)-1-(1,2,2-trifluorovinyloxy)benzene was dropped in a mixture of 2.5 g (0.11 mols) of magnesium and 300 ml of THF to obtain a Grignard reagent. The resultant solution was then dropped in a solution, in 500 ml of THF, of 0.5 g of triethyl phosphate, 0.1 g of copper (I) iodide and 29.1 g (0.1 mol) of trans-4-(4-bromobutyl)-1-n-butyl-1-silacyclohexane. The resultant product consisted of a mixture of tram and cis isomers with respect to the cyclohexane ring. The product was subjected to ordinary aftertreatments to obtain trans-4-(4-(trans-4-(1,2,2-trifluorovinyloxy)phenyl)cyclohexyl)butyl)-1-n-butyl-1-silacyclohexane, followed by isolation through chromatography to obtain 17.1 g (yield: 37%) of the intended trans isomer product.

Sources & evidence

ORD record
ord-c6c3cd18dbee4b3ba103e141452faad9
Source dataset
uspto-grants-1997_09
Patent number
US05665271

Reaction notes

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