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

HRID 2601

反応式

HRID 2601 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3fd18c20fe384f209c75449594a77dfc
出典データセット
uspto-grants-1998_03
特許番号
US05728370

関連ノート

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