Reaction #48617

Reaction equation

sodium chloride

[(R)-1-(tert-butyl-dimethylsilanyloxymethyl)-2-hydroxyethyl]-carbamic acid tert-butyl ester

ethyl vinyl ether

acetonitrile

N-iodosuccinimide

→

desired compound

Yield 34.0%

[(R)-2-(tert-butyl-dimethylsilanyloxy)-1-(1-ethoxy-2-iodoethoxymethyl)-ethyl]-carbamic acid tert-butyl ester

Yield 34.0%

Conditions

Workup

1. 1
   ExtractionExtract with ethyl acetate
2. 2
   Washwash with water and saturated aqueous sodium chloride
3. 3
   Dryingdry (magnesium sulfate)
4. 4
   Filtrationfilter
5. 5
   Concentrationconcentrate
6. 6
   OtherPurify
7. 7
   Wash(silica gel chromatography, eluting with 100:0 to 10:90 hexanes:ethyl acetate)

Procedure

Dissolve [(R)-1-(tert-butyl-dimethylsilanyloxymethyl)-2-hydroxyethyl]-carbamic acid tert-butyl ester (1.0 g, 3.27 mmol) and ethyl vinyl ether (0.20 g, 2.73 mmol) in acetonitrile (20 mL) and add N-iodosuccinimide (0.735 g, 3.27 mmol). Stir at room temperature 72 hours and pour into saturated aqueous sodium chloride. Extract with ethyl acetate, wash with water and saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify (silica gel chromatography, eluting with 100:0 to 10:90 hexanes:ethyl acetate) to give the desired compound (462 mg, 34%).

Source