반응 #2488537

반응 방정식

sodium azide

(4-chlorophenyl)(2-(3-(1-hydroxyethyl)-5-methylisoxazol-4-yl)phenyl)methanone

Et3N

methanesulfonyl chloride

→

(2-(3-(1-azidoethyl)-5-methylisoxazol-4-yl)phenyl)(4-chlorophenyl)methanone

수율 74.0%

용매

water

EtOAc

CH2Cl2

반응 조건

후처리

1. 1
   기타before quenching with water
2. 2
   기타The layers were separated
3. 3
   추출the aqueous extracted with CH2Cl2
4. 4
   건조The combined organics were dried over Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated
7. 7
   workup.STIRRINGThe reaction was stirred at room temperature overnight
8. 8
   기타The layers were separated
9. 9
   추출the aqueous was extracted with EtOAc
10. 10
    세척The combined organics were washed with brine
11. 11
    건조dried over Na2SO4
12. 12
    여과filtered
13. 13
    농축concentrated
14. 14
    기타The crude residue was purified via Biotage (EtOAc/hex)

실험 절차

To a round bottomed flask was added (4-chlorophenyl)(2-(3-(1-hydroxyethyl)-5-methylisoxazol-4-yl)phenyl)methanone (0.092 g, 0.269 mmol), CH2Cl2 (3.0 mL), and Et3N (0.075 mL, 0.538 mmol). The vial was cooled to 0° C. before addition of methanesulfonyl chloride (0.025 mL, 0.323 mmol) and the reaction stirred for 45 min at 0° C. before quenching with water. The layers were separated and the aqueous extracted with CH2Cl2. The combined organics were dried over Na2SO4, filtered, and concentrated. The crude residue was taken up in DMF (2 mL) and sodium azide (0.053 g, 0.808 mmol) was added. The reaction was stirred at room temperature overnight before being diluted with water and EtOAc. The layers were separated and the aqueous was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (2-(3-(1-azidoethyl)-5-methylisoxazol-4-yl)phenyl)(4-chlorophenyl)methanone (0.073 g, 0.199 mmol). LC/MS m/z 389 [M+Na]+.

출처