Triethyl Phosphate → HCID 178447966, compound

HRID 1377408Notes

Reaction equation

HRID 1377408 reaction equation
P(O[CH2:10][CH3:11])(OCC)(OCC)=O.Br[CH2:13][CH2:14][CH2:15][Si@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]2[CH:27]=[C:26]([F:28])[C:25]([C:29]([F:32])([F:31])[F:30])=[C:24]([F:33])[CH:23]=2)[CH2:18][CH2:17]1>C1COCC1.[Cu]I>[F:33][C:24]1[CH:23]=[C:22]([C@H:19]2[CH2:20][CH2:21][Si@H:16]([CH2:15][CH2:14][CH2:13][CH2:19][C@H:22]3[CH2:27][CH2:26][C@H:25]([CH2:29][CH2:10][CH3:11])[CH2:24][CH2:23]3)[CH2:17][CH2:18]2)[CH:27]=[C:26]([F:28])[C:25]=1[C:29]([F:32])([F:31])[F:30]

Participants

5

Reactant 2

HCID 6535Triethyl PhosphateHCID 178505817HCID 178505817, compound

Product 1

HCID 178447966HCID 178447966, compoundYield 81%

Reagents, catalysts & solvents 2

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

Procedure

21.9 g (0.1 mol) of trans-4-bromomethyl-1-n-propyl-1-silacyclohexane 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 40.1 g (0.1 mol) of 4-(trans-4-(3-bromopropyl)-4-silacyclohexyl) -2,6-difluoro-1-trifluormethylbenzene. The resultant product was subjected to ordinary aftertreatments to obtain trans-4-(4-(trans-4-(3,5-difluoro-4-trifluoromethylphenyl)-1-silacyclohexyl)butyl)-1 -n-propylcyclohexane, followed by isolation through chromatography to obtain 37.2 g (yield: 81%) of the intended trans isomer product.

Sources & evidence

ORD record
ord-440fbe21f0ab43349fdedf592c20474c
Source dataset
uspto-grants-1997_09
Patent number
US05665271

Reaction notes

Loading…