Chlorotrimethylgermane → 2-(3-Trimethylgermylphenyl)-2-methyl-1,3-dioxolane

HRID 613175Notes

Reaction equation

HRID 613175 reaction equation
[Mg].[CH3:2][Ge:3](Cl)([CH3:5])[CH3:4].Br[C:8]1[CH:9]=[C:10]([C:14]2([CH3:19])[O:18][CH2:17][CH2:16][O:15]2)[CH:11]=[CH:12][CH:13]=1>O1CCCC1>[CH3:2][Ge:3]([CH3:5])([CH3:4])[C:8]1[CH:9]=[C:10]([C:14]2([CH3:19])[O:18][CH2:17][CH2:16][O:15]2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 73723ChlorotrimethylgermaneHCID 5462224MagnesiumHCID 109992182-(3-Bromophenyl)-2-methyl-1,3-dioxolane

Product 1

HCID 146056542-(3-Trimethylgermylphenyl)-2-methyl-1,3-dioxolaneYield 103.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 81 mg (3.33 mmol) of magnesium and 574 mg (3.75 mmol) of trimethylgermyl chloride was stirred at 40°-50° C. in an atmosphere of argon. To the mixture was added a solution of 729 mg (3.00 mmol) of 2-(3-bromophenyl)-2-methyl-1,3-dioxolane in 10 ml of tetrahydrofuran with stirring. The mixture was refluxed for 2.5 hr. and stirred at room temperature overnight. To the reaction mixture was added petroleum ether and the insoluble substance was filtered off. The filtrate was evaporated to give 874 mg of pale yellow crystals, which were purified by column chromatography on silica gel [eluent: methylene chloride-n-hexane (1:1)] to give 657 mg of white cubes, m.p. 62.5°-63.5° C. (yield 78%).

Workup

  1. stirringwith stirring
  2. temperatureThe mixture was refluxed for 2.5 hr
  3. stirringand stirred at room temperature overnight
  4. filtrationthe insoluble substance was filtered off
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-6a0b0bfe20254724a8303a042a4c19ad
Source dataset
uspto-grants-1999_12
Patent number
USRE036477

Reaction notes

Loading…