Reaktion #742907

Reaktionsgleichung

(R)-methyl oxirane-2-carboxylate

Magnesium trifluoromethanesulfonate

(S)-1-(triisopropylsilyloxy)propan-2-ol

(R)-methyl oxirane-2-carboxylate

(R)-methyl oxirane-2-carboxylate

→

product

Ausbeute 41.2%

(R)-methyl 2-hydroxy-3-((S)-1-(triisopropylsilyloxy)propan-2-yloxy)propanoate

Ausbeute 41.2%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture stirred for 24 hrs
2. 2
   Temperaturto cool
3. 3
   Filtrationfiltered through a bed of silica (˜10 g)
4. 4
   Waschenwashed through with EtOAc
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe crude product was purified by flash silica chromatography, elution gradient 10 to 50% EtOAc in isohexane

Vorschrift

Magnesium trifluoromethanesulfonate (1.263 g, 3.92 mmol) was added to a mixture of (S)-1-(triisopropylsilyloxy)propan-2-ol (4.55 g, 19.59 mmol) and (R)-methyl oxirane-2-carboxylate (2 g, 19.59 mmol) in ethyl acetate (40 mL). The resulting suspension was heated to 80° C. for 72 hours. Further (R)-methyl oxirane-2-carboxylate (2 g, 19.59 mmol) was added and the mixture stirred at 80° C. for 48 hrs. Further (R)-methyl oxirane-2-carboxylate (2 g, 19.59 mmol) was added and the mixture stirred for 24 hrs. The mixture was allowed to cool, filtered through a bed of silica (˜10 g), washed through with EtOAc and evaporated. The crude product was purified by flash silica chromatography, elution gradient 10 to 50% EtOAc in isohexane, to afford the product (2.7 g, 41%).

Quelle