반응 #68907

반응 방정식

(R)-glycidyl 3-nitrobenzene sulfonate

Sodium hydride

4-hydroxy indole

→

title compound

4-Oxiranylmethoxy-1-H-indole

용매

heptane

ethyl acetate

ethyl acetate

dimethylformamide

ethyl acetate

반응 조건

후처리

1. 1
   workup.ADDITIONAfter 3 hour the reaction mixture was poured into a separatory funnel
2. 2
   세척The organic layer was washed 3 times with a 10% solution of sodium carbonate in water
3. 3
   건조the organic layer was dried with sodium sulfate
4. 4
   기타the solvent was removed by reduced pressure
5. 5
   기타to yield crude product
6. 6
   workup.ADDITIONCelite® (approximately 3 grams) was added
7. 7
   기타followed by removal of the solvent under reduced pressure
8. 8
   기타The Celite®/reaction mixture
9. 9
   온도increasing
10. 10
    농축the ethyl acetate concentration to 60% over 40 column volumes

실험 절차

4-hydroxy indole (0.08 g, mmol) was dissolved in dimethylformamide (1.5 mL). Sodium hydride (0.02 g, 0.51 mmol) was slowly added to the reaction mixture followed by addition of (R)-glycidyl 3-nitrobenzene sulfonate (0.132, 0.51 mmol). A red color appeared. After 3 hour the reaction mixture was poured into a separatory funnel and ethyl acetate (100 mL) was added. The organic layer was washed 3 times with a 10% solution of sodium carbonate in water. The aqueous layers were discarded, the organic layer was dried with sodium sulfate and the solvent was removed by reduced pressure to yield crude product. The crude product was dissolved in ethyl acetate, Celite® (approximately 3 grams) was added, followed by removal of the solvent under reduced pressure. The Celite®/reaction mixture was loaded into an Isco solid phase loading cartridge. Flash chromatography was carried out using an Isco Companion automated chromatography system, silica column (4 g), initially holding at 5% ethyl acetate in heptane for 3 column volumes, increasing the ethyl acetate concentration to 60% over 40 column volumes, holding at 60% ethyl acetate for 10 more column volumes to yield the title compound as a residue.

출처