Pyridine → HCID 13339032, compound

HRID 1982350Notes

Reaction equation

HRID 1982350 reaction equation
N1C=CC=CC=1.[S:7]([O:17][CH:18]([CH3:22])[C:19](Cl)=[O:20])([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8].[CH3:23][Si:24]([CH2:27][OH:28])([CH3:26])[CH3:25].C1(C)C=CC=CC=1>O>[S:7]([O:17][CH:18]([CH3:22])[C:19]([O:28][CH2:27][Si:24]([CH3:26])([CH3:25])[CH3:23])=[O:20])([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 766921-(Trimethylsilyl)methanolHCID 12761564HCID 12761564, compound

Product 1

HCID 13339032HCID 13339032, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

33 g (0.41 mole) of pyridine are slowly added dropwise to a mixture of 109 g (0.41 mole) of the S-enantiomer of tosyloxy-propionic acid chloride, 43.4 g (0.41 mole) of trimethylsilyl-methanol and 250 ml of toluene at 20° C., with stirring. The mixture is subsequently stirred at room temperature for 24 hours. Working up is then carried out by a procedure in which the reaction mixture is poured into water and extracted with toluene and the organic phase is concentrated by stripping off the diluent under reduced pressure. 130 g (96% of theory) of the S-enantiomer of trimethylsilyl-methyl 2-tosyloxy-propionate are obtained in this manner in the form of an oily product.

Workup

  1. stirringThe mixture is subsequently stirred at room temperature for 24 hours
  2. extractionextracted with toluene
  3. concentrationthe organic phase is concentrated

Sources & evidence

ORD record
ord-ed216a185d9c42df9bc9d9ea41b5717e
Source dataset
uspto-grants-1986_06
Patent number
US04596594

Reaction notes

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