반응 #51860

반응 방정식

Water

triethylamine

(2-chlorosulfonyl-4,5-dimethoxy-phenyl)-acetic acid benzyl ester

morpholine

→

title compound

수율 60.2%

[4,5-Dimethoxy-2-(morpholine-4-sulfonyl)-phenyl]-acetic acid benzyl ester

수율 60.2%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타to form a solid mass
2. 2
   workup.ADDITIONwas added
3. 3
   온도the mixture was warmed to ambient temperature over 20 hours
4. 4
   추출extracted with ethyl acetate (2×100 cm3)
5. 5
   건조The combined ethyl acetate extracts were dried over sodium sulfate, vacuum
6. 6
   여과filtered
7. 7
   기타the filtrate volatile fractions removed in vacuo
8. 8
   기타to afford a crude tan solid
9. 9
   기타The crude solid was recrystallized from toluene (150 cm3)

실험 절차

To a stirred mixture of (2-chlorosulfonyl-4,5-dimethoxy-phenyl)-acetic acid benzyl ester (15.0 g, 39.0 mmol) in anhydrous tetrahydrofuran (45 cm3) cooled to 0° C. in an ice bath under an atmosphere of dry nitrogen was added triethylamine (6.00 cm3, 43 mmol). The mixture was stirred 2 minutes and morpholine (3.75 cm3, 43 mmol) was added dropwise to form a solid mass. To efficiently stir the mixture additional anhydrous tetrahydrofuran (145 cm3) was added and the mixture was warmed to ambient temperature over 20 hours. Water was added to the mixture and extracted with ethyl acetate (2×100 cm3). The combined ethyl acetate extracts were dried over sodium sulfate, vacuum filtered and the filtrate volatile fractions removed in vacuo to afford a crude tan solid. The crude solid was recrystallized from toluene (150 cm3) to afford the title compound as tan crystals (10.2 g, 60.2%) with a positive ion ESI (M+H)+436.2.

출처