Pyridine → t-Butyl 2-mesyloxypropionate

HRID 434713Notes

Reaction equation

HRID 434713 reaction equation
[S:1]([O:5][CH:6]([CH3:10])[C:7]([OH:9])=[O:8])([CH3:4])(=[O:3])=[O:2].P(Cl)(Cl)(Cl)=O.[CH2:16](Cl)Cl.N1[CH:24]=[CH:23][CH:22]=CC=1>C(O)(C)(C)C>[S:1]([O:5][CH:6]([CH3:10])[C:7]([O:9][C:23]([CH3:22])([CH3:24])[CH3:16])=[O:8])([CH3:4])(=[O:3])=[O:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 24813Phosphorus oxychlorideHCID 127615472-((Methylsulfonyl)oxy)propanoic acid

Product 1

HCID 20491922t-Butyl 2-mesyloxypropionate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
-5 °C

Procedure

0.35 mole of the S optical isomer of 2-mesyloxypropionic acid was dissolved in 25 ml of pyridine and 500 ml of t-butanol, and 65 g of phosphoryl chloride was added, with stirring, at -5° C. After a further 30 minutes stirring at -5° C., and a further 2 hours at 20° C., the mixture was poured into ice-water, and methylene chloride was added. The organic layer was washed successively with dilute hydrochloric acid, sodium bicarbonate, and water, and then evaporated to give a solid which was recrystalised from light petroleum ether to give (S) t-butyl 2-mesyloxypropionate.

Workup

  1. stirringAfter a further 30 minutes stirring at -5° C.
  2. additionwas added
  3. washThe organic layer was washed successively with dilute hydrochloric acid, sodium bicarbonate, and water
  4. customevaporated
  5. customto give a solid which
  6. customwas recrystalised from light petroleum ether

Sources & evidence

ORD record
ord-90b17078cbb44ab485a3538ccd38833a
Source dataset
uspto-grants-1983_08
Patent number
US04399149

Reaction notes

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