Chlorotrimethylsilane → 8-Trimethylsilyl-2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiole

HRID 1108175Notes

Reaction equation

HRID 1108175 reaction equation
[CH3:1][C:2]1([CH3:16])[S:6][C:5]2=[CH:7][C:8]3[S:9][C:10]([CH3:15])([CH3:14])[O:11][C:12]=3[CH:13]=[C:4]2[O:3]1.C([Li])CCC.Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[CH3:24][Si:23]([CH3:26])([CH3:25])[C:13]1[C:4]2[O:3][C:2]([CH3:16])([CH3:1])[S:6][C:5]=2[CH:7]=[C:8]2[S:9][C:10]([CH3:15])([CH3:14])[O:11][C:12]=12

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 187852282,2,6,6-Tetramethylbenzo[1,2-d:5,4-d']bis(1,3)oxathioleHCID 178418339Butyllithium

Product 1

HCID 187852378-Trimethylsilyl-2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was performed under an argon atmosphere using deoxygenated solvents. 2,2,6,6-tetramethylbenzo[1,2-d:5,4-d']-bis(1,3)oxathiole (6.0 g, 23.6 mmol) was dissolved in dry THF (120 mL). The mixture was cooled on an ice-bath and n-butyllithium (10.8 mL, 2.5M in hexane) was added dropwise over 10 min. After 15 min, chlorotrimethylsilane (6.0 mL, 47.2 mmol) was added dropwise over 5 min. After another 15 min, the reaction mixture was quenched with dietyl ether/aq. NaHCO3, the aqueous layer was extracted with ether and the combined organic layers were washed with water and dried (Na2SO4). After evaporation and chromatography (silica gel, chloroform) essentially pure product (6.3 g, 92%) could be collected.

Workup

  1. customusing deoxygenated solvents
  2. temperatureThe mixture was cooled on an ice-bath
  3. waitAfter another 15 min
  4. customthe reaction mixture was quenched with dietyl ether/aq
  5. extractionNaHCO3, the aqueous layer was extracted with ether
  6. washthe combined organic layers were washed with water
  7. dry with materialdried (Na2SO4)
  8. customAfter evaporation and chromatography (silica gel, chloroform) essentially pure product (6.3 g, 92%)
  9. customcould be collected

Sources & evidence

ORD record
ord-a834db7db23c49a7b42501db775b9c6d
Source dataset
uspto-grants-2000_05
Patent number
US06063360

Reaction notes

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