تفاعل #68910

معادلة التفاعل

sodium carbonate

2-Methyl-1H-indol-4-ol

Sodium bis(trimethylsilyl) amide

(R)-glycidyl-3-nitrobenzenesulfonate

→

title compound

(S)-2-Methyl-4-oxiranylmethoxy-1H-indole

المذيبات

THF

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGto stir overnight
3. 3
   تجفيفThe organic layer was dried with sodium sulfate
4. 4
   ترشيحfiltered
5. 5
   أخرىthe solvent was removed under reduced pressure
6. 6
   أخرىto yield a crude oil
7. 7
   أخرىThe crude oil was purified by flash chromatography (20% Ethyl acetate/heptane)

الإجراء التجريبي

2-Methyl-1H-indol-4-ol (0.58 g, 3.9 mmol) and THF (20 mL) were placed in a round bottom flask and stirred at room temperature. Sodium bis(trimethylsilyl) amide (3.9 mL, [1M] in THF) was then slowly added to the reaction mixture. After fifteen minutes of stirring at room temperature (R)-glycidyl-3-nitrobenzenesulfonate was added and the reaction mixture was allowed to stir overnight. Work up of the reaction mixture was carried out with saturated sodium carbonate solution and ethyl acetate. The organic layer was dried with sodium sulfate, filtered and the solvent was removed under reduced pressure to yield a crude oil. The crude oil was purified by flash chromatography (20% Ethyl acetate/heptane) to yield the title compound as a crystalline solid.

المصدر