Benzene, (2-iodoethyl)- → HCID 178460921, compound

HRID 1077606Notes

Reaction equation

HRID 1077606 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][Si@H:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[CH:2].I[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.C(N(CC)CC)C>[CH2:15]([Si@H:12]1[CH2:11][CH2:10][C@H:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:24]3[CH:25]=[CH:26][C:21]([CH2:20][CH3:19])=[CH:22][CH:23]=3)=[CH:4][CH:5]=2)[CH2:14][CH2:13]1)[CH2:16][CH3:17]

Participants

6

Reactant 2

HCID 28503Benzene, (2-iodoethyl)-HCID 178436320HCID 178436320, compound

Product 1

HCID 178460921HCID 178460921, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

100 mg of tetrakis (triphenylphosphine) palladium (0) and 50 mg of copper (I) iodide were added to a mixture of 1.21 g (5.00 mmol) of trans-4-(p-ethynylphenyl)-1-n-propyl-1-silacyclohexane, 1.50 g (6.46 mmol) of p-iodoethylbenzene and 30 ml of triethylamine. The reaction mixture was stirred for 20 hours at room temperature. After a conventional after treatment, purification was conducted by means of silica-gel column chromatography to obtain 1.30 g (yield 75%) of the target product.

Workup

  1. customAfter a conventional after treatment, purification

Sources & evidence

ORD record
ord-6a98463a8d314cff8c1cd6d3491305d2
Source dataset
uspto-grants-1996_08
Patent number
US05543539

Reaction notes

Loading…