Hydrochloric Acid → HCID 19757560, compound

HRID 1587262Notes

Reaction equation

HRID 1587262 reaction equation
[CH2:1]([Si:5]([CH3:11])([CH3:10])[CH2:6][CH2:7][CH2:8][OH:9])[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1.Cl>O>[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24]([O:9][CH2:8][CH2:7][CH2:6][Si:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH3:10])[CH3:11])(=[O:26])=[O:25])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 197575723-[Butyl(dimethyl)silyl]propan-1-ol

Product 1

HCID 19757560HCID 19757560, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g (28.68 mM) of butyldimethyl-3-hydroxypropylsilane was added 50 ml of pyridine, followed by stirring. To the mixture, 5.4 g (28.32 mM) of p-toluenesulfonyl chloride was added under cooling on an ice bath, followed by stirring for 0.5 hour and further stirring for 4 hours at room temperature. After the reaction, the reaction mixture was poured into water, acidified with hydrochloric acid (pH≈2) and extracted with ethyl acetate, followed by washing with water and drying with anhydrous magnesium sulfate. The magnesium sulfate in the resultant mixture was filtered off and the filtrate was condensed into a solid to obtain 3-(butyldimethylsilyl)propyl p-toluenesulfonate (Yield: 81.7 %).

Workup

  1. temperatureunder cooling on an ice bath
  2. stirringby stirring for 0.5 hour
  3. stirringfurther stirring for 4 hours at room temperature
  4. customAfter the reaction
  5. extractionextracted with ethyl acetate
  6. washby washing with water
  7. dry with materialdrying with anhydrous magnesium sulfate
  8. filtrationThe magnesium sulfate in the resultant mixture was filtered off
  9. customcondensed into a solid

Sources & evidence

ORD record
ord-ea5a4a9aa6c842c6a3bf55b4d6557101
Source dataset
uspto-grants-1993_06
Patent number
US05217645

Reaction notes

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