Reaction #1509615

Reaction equation

Ethyl chloroformate

Na2CO3

DI water

THF

serinol

DI water

→

solid

Yield 54.5%

ethyl 1,3-dihydroxypropan-2-yl-carbamate

Yield 54.5%

Conditions

Workup

1. 1
   Temperatureto cool in ice
2. 2
   workup.WAITfollowed by about 16 hours at room temperature
3. 3
   Extractionthe product was extracted into ethyl acetate (20×100 mL)
4. 4
   OtherThe crude product (11.6 g) was further purified by flash column chromatography
5. 5
   Otherwas crystallized in the presence of trace ethyl acetate (1 to 2 mL) along
6. 6
   WashThe crystallized product was washed with cold ethyl acetate:hexanes (1:1) mixture (1×100 mL)
7. 7
   Otherdried under vacuum

Procedure

In a 1 liter round bottom flask with magnetic stir bar, serinol (10.0 g) and Na2CO3 (25.0 g) were dissolved in the mixture of DI water (250 mL) and THF (150 mL). The reaction mixture was allowed to cool in ice. Ethyl chloroformate (10.5 mL) was added drop-wise and the reaction was allowed to proceed in ice for 4 hours, followed by about 16 hours at room temperature. Another 100 mL of DI water was added to the reaction mixture and the product was extracted into ethyl acetate (20×100 mL). The crude product (11.6 g) was further purified by flash column chromatography, using silica as the packing material and CH3OH:CHCl3 (1:9) mixture as the eluent. The final product was a transparent viscous oil that was crystallized in the presence of trace ethyl acetate (1 to 2 mL) along with vigorous scratching using a spatula. The crystallized product was washed with cold ethyl acetate:hexanes (1:1) mixture (1×100 mL), and dried under vacuum to result in white crystalline solid (8.9 g, 54.5%).

Source