Pyridine → 2-(Trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate

HRID 1025419Notes

Reaction equation

HRID 1025419 reaction equation
[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](Cl)=[O:9])(=[O:4])=[O:3].N1C=CC=CC=1.ClCCl.[CH3:23][Si:24]([CH3:29])([CH3:28])[CH2:25][CH2:26][OH:27]>O>[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:27][CH2:26][CH2:25][Si:24]([CH3:29])([CH3:28])[CH3:23])=[O:9])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 180132-(Trimethylsilyl)ethanolHCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-

Product 1

HCID 866763342-(Trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 23.9 g of 3-(chlorosulfonyl)benzoyl chloride, 7.9 mL of pyridine, and 100 mL of dichloromethane was added dropwise 14 mL of 2-(trimethylsilyl)ethanol under ice-cooling, followed by stirring at room temperature for 2 hours. To the reaction mixture was added water, followed by extraction with chloroform, and the organic layer was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 29.4 g of 2-(trimethylsilyl)ethyl 3-(chlorosulfonyl)benzoate as a colorless solid.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with chloroform
  3. concentrationthe organic layer was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-506b5c42f20041ad859001f4cb5c834c
Source dataset
uspto-grants-2014_05
Patent number
US08729068B2

Reaction notes

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