Reaction #949

Reaction equation

HCl

pyridine

Tosyl chloride

product

(+-)-Ethyl-4-(hydroxymethyl)-2-oxazolidinone

→

beige solid

(+-)-4-Ethyl-4-[(tosyloxy)methyl]-2-oxazolidinone

Solvents

brine

Conditions

Workup

1. 1
   Otherto come to room temperature
2. 2
   workup.STIRRINGstirred until solids
3. 3
   Filtrationfiltered
4. 4
   Washwashed with diethyl ether

Procedure

Tosyl chloride (142.2 g, Aldrich) was added to an ice-chilled solution of the product from step (a) (102.7 g) dissolved in pyridine (175 ml. Aldrich). The reaction mixture was stirred at ice bath temperature for six hours, then allowed to come to room temperature. The heterogeneous mixture was added to 1500 ml of a solution of brine and 1N HCl, stirred until solids appeared, filtered and washed with diethyl ether to give 194.6 g of a beige solid as the title product. 1H NMR consistent with the proposed structure.

Source