Chlorotrimethylgermane → 2-(4-Trimethylgermylphenyl)-2-methyl-1,3-dioxolane

HRID 613161

Reaction equation

HRID 613161 reaction equation
[Mg].[CH3:2][Ge:3](Cl)([CH3:5])[CH3:4].Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]2([CH3:19])[O:18][CH2:17][CH2:16][O:15]2)=[CH:10][CH:9]=1>O1CCCC1>[CH3:2][Ge:3]([CH3:5])([CH3:4])[C:8]1[CH:13]=[CH:12][C:11]([C:14]2([CH3:19])[O:18][CH2:17][CH2:16][O:15]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 73723ChlorotrimethylgermaneHCID 6149202-(4-Bromophenyl)-2-methyl-1,3-dioxolaneHCID 5462224Magnesium

Product 1

HCID 146056512-(4-Trimethylgermylphenyl)-2-methyl-1,3-dioxolaneYield 46.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 108 mg (4.44 mmol) of magnesium and 766 mg (5.00 mmol) of trimethylgermyl chloride was added a solution of 972 mg (4.00 mmol) of 2-(4-bromophenyl)-2-methyl-1,3-dioxolane in 12 ml of dry tetrahydrofuran (THF) at 40° C. with stirring. The mixture was refluxed for 1.5 hours and stirred at room temperature overnight. An insoluble substance was filtered off and washed with ether. The filtrate and washings were mixed and evaporated. The residue was purified by column chromatography on silica gel [eluent: petroleum ether-methylene chloride (2:1-1:2)] and recrystallized from petroleum ether to give 524 mg of white prisms, m.p. 63.5°-65° C.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. stirringstirred at room temperature overnight
  3. filtrationAn insoluble substance was filtered off
  4. washwashed with ether
  5. additionThe filtrate and washings were mixed
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel [eluent: petroleum ether-methylene chloride (2:1-1:2)]
  8. customrecrystallized from petroleum ether

Sources & evidence

ORD record
ord-52d40f97a4844656a56177e0f4835b00
Source dataset
uspto-grants-1999_12
Patent number
USRE036477

Linked notes

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