Tetramethoxysilane → 2-(Trimethoxysilyl)thianthrene

HRID 716587Notes

Reaction equation

HRID 716587 reaction equation
[Mg].[CH3:2][O:3][Si:4](OC)([O:7][CH3:8])[O:5][CH3:6].Br[C:12]1[CH:25]=[CH:24][C:23]2[S:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[S:15][C:14]=2[CH:13]=1>C1COCC1>[CH3:2][O:3][Si:4]([O:7][CH3:8])([O:5][CH3:6])[C:12]1[CH:25]=[CH:24][C:23]2[S:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[S:15][C:14]=2[CH:13]=1

Participants

5

Reactant 3

HCID 12682TetramethoxysilaneHCID 5462224MagnesiumHCID 132131222-Bromothianthrene

Product 1

HCID 711166972-(Trimethoxysilyl)thianthreneYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 3-neck 1 L flask was filled with magnesium turnings (5 g), THF (200 g) and tetramethoxysilane (50 g), and heated to reflux. 2-Bromothianthrene (40 g), prepared analogously to Example 3A was added to the flask in 10 g portions. Grignard started within 10 minutes. The reaction was allowed to cool for 1 hour, after which magnesium salts were precipitated with hexanes (200 mL). GC/MS of the solution showed that along with some thianthrene, 2-(trimethoxysilyl)thianthrene was obtained in ˜60% yield (FIG. 7).

Workup

  1. temperatureheated to reflux
  2. additionwas added to the flask in 10 g portions
  3. temperatureto cool for 1 hour
  4. customafter which magnesium salts were precipitated with hexanes (200 mL)

Sources & evidence

ORD record
ord-c3be22e915f540efa35b32c846145ac7
Source dataset
uspto-grants-2015_11
Patent number
US09190616B2

Reaction notes

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