Sodium Chloride → (NE,S)-N-[1-[tert-butyl(dimethyl)silyl]oxypropan-2-ylidene]-2-methylpropane-2-sulfinamide

HRID 923501ノート

反応式

HRID 923501 の反応式
[C:1]([Si:5]([CH3:12])([CH3:11])[O:6][CH2:7][C:8]([CH3:10])=O)([CH3:4])([CH3:3])[CH3:2].[CH3:13][C:14]([S@@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15].[Cl-].[Na+]>C1COCC1.CCO.CCO.CCO.CCO.[Ti]>[Si:5]([O:6][CH2:7]/[C:8](=[N:19]/[S@:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])/[CH3:10])([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:12])[CH3:11]

参加物

6

反応物 3

HCID 5234Sodium ChlorideHCID 41249691-(tert-Butyldimethylsilyloxy)-2-propanoneHCID 11355477tert-Butylsulfinamide, (S)-(-)-

生成物 1

HCID 90089971(NE,S)-N-[1-[tert-butyl(dimethyl)silyl]oxypropan-2-ylidene]-2-methylpropane-2-sulfinamide

試薬・触媒・溶媒 2

HCID 2724286Titanium(IV)ethoxide触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

To a solution of 761 mg of 1-{[tert-butyl (dimethyl)silyl]oxy}acetone in 20 ml of THF were added 2.1 ml of tetraethyl orthotitanate and 490 mg of (S)-2-methylpropane-2-sulfinamide, followed by stirring at 70° C. for 8 hours. The reaction mixture was left to be cooled to room temperature and a saturated aqueous sodium chloride solution was then added thereto, followed by stirring and filtering over Celite. The filtrate was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain (S)—N-[(2E)-1-{[tert-butyl(dimethyl)silyl]oxy}propan-2-ylidene]-2-methylpropane-2-sulfinamide.

後処理

  1. waitThe reaction mixture was left
  2. temperatureto be cooled to room temperature
  3. stirringby stirring
  4. filtrationfiltering over Celite
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was then evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-81a2ccdcebbb4547ac546954f461f188
出典データセット
uspto-grants-2016_03
特許番号
US09278968B2

反応ノート

読み込み中…