Triethyl Phosphate → HCID 178447774, compound

HRID 1377404Notes

Reaction equation

HRID 1377404 reaction equation
P(O[CH2:10][CH3:11])(OCC)(OCC)=O.Br[CH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([C@H:20]2[CH2:25][CH2:24][Si@H:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:22][CH2:21]2)[CH2:16][CH2:15]1>C1COCC1.[Cu]I>[CH2:20]([C:17]1[CH:18]=[CH:19][C:14]([CH2:13][CH2:10][CH2:11][CH2:13][C@H:14]2[CH2:19][CH2:18][C@H:17]([C@H:20]3[CH2:25][CH2:24][Si@H:23]([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:22][CH2:21]3)[CH2:16][CH2:15]2)=[CH:15][CH:16]=1)[CH3:21]

Participants

5

Reactant 2

HCID 6535Triethyl PhosphateHCID 178447767HCID 178447767, compound

Product 1

HCID 178447774HCID 178447774, compoundYield 79%

Reagents, catalysts & solvents 2

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

Procedure

22.7 g (0.1 mol) of 4-(3-bromopropyl)-1-ethylbenzene 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 further dropped in a solution, in 500 ml of THF, of 0.5 g of triethyl phosphate, 0.1 g of copper (I) iodide and 34.5 g (0.1 mol) of trans-4-(trans-4-bromomethylcyclohexyl)-1-pentyl-1-silacyclohexane. The resultant product was subjected to ordinary aftertreatments to obtain trans-4-(trans-4-(4-(4-ethylphenyl)butyl)cyclohexyl)-1-pentyl-1-silacyclohexane. After ordinary aftertreatments, the product was purified through chromatography to obtain 32.6 g (yield: 79%) of the trans isomer product.

Sources & evidence

ORD record
ord-b41aaa1dec194cf78e74012067245cf9
Source dataset
uspto-grants-1997_09
Patent number
US05665271

Reaction notes

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