Tetrahydrofuran → HCID 178447758, compound

HRID 1080594Notes

Reaction equation

HRID 1080594 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Mg].[CH2:12]1COC[CH2:13]1.CO[CH2:19][CH2:20][CH2:21][Si@H:22]1[CH2:27][CH2:26][C@H:25]([CH2:28][CH2:29][C@H:30]2[CH2:35][CH2:34][C@H:33]([C:36]3[CH:41]=[CH:40][C:39](Cl)=[CH:38][CH:37]=3)[CH2:32][CH2:31]2)[CH2:24][CH2:23]1>Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)C>[CH2:21]([Si@H:22]1[CH2:27][CH2:26][C@H:25]([CH2:28][CH2:29][C@H:30]2[CH2:35][CH2:34][C@H:33]([C:36]3[CH:41]=[CH:40][C:39]([C:8]4[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH3:2])=[CH:6][CH:7]=4)=[CH:38][CH:37]=3)[CH2:32][CH2:31]2)[CH2:24][CH2:23]1)[CH2:20][CH2:19][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 12156Benzene, (2-chloroethoxy)-HCID 5462224MagnesiumHCID 178495611HCID 178495611, compound

Product 1

HCID 178447758HCID 178447758, compoundYield 67.5%

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

15.7 g (0.1 mol) of p-chloroethoxybenzene was dripped into a mixture of 2.5 g (0.11 mol) of magnesium and 100 ml of THF to obtain a Grignard's reagent. This solution was then dripped into a 100 ml diethyl ether solution of 0.5 g of [1,3-bis(diphenylphosphino)propane]nickel (II) chloride and 31.5 g (0.1 mol) of 4-(trans-4-(2-(trans-4-(3-methoxypropyl)-4-silacyclohexyl)ethyl)cyclohexyl)phenyl chloride. After a conventional after treatment, purification was conducted by means of chromatography to obtain 32.2 g (yield 67.5%) of 4-(trans-4-(2-(trans-4-n-pentyl-4-silacyclohexyl)ethyl)cyclohexyl)-4'-ethoxybiphenyl was obtained.

Workup

  1. customto obtain a Grignard's reagent
  2. customAfter a conventional after treatment, purification

Sources & evidence

ORD record
ord-d22d246983c44fc0915d90758120cbb6
Source dataset
uspto-grants-1996_12
Patent number
US05582764

Reaction notes

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