反応 #51860

反応方程式

Water

triethylamine

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

morpholine

→

title compound

収率 60.2%

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

収率 60.2%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他to form a solid mass
2. 2
   workup.ADDITIONwas added
3. 3
   温度the mixture was warmed to ambient temperature over 20 hours
4. 4
   抽出extracted with ethyl acetate (2×100 cm3)
5. 5
   乾燥The combined ethyl acetate extracts were dried over sodium sulfate, vacuum
6. 6
   ろ過filtered
7. 7
   その他the filtrate volatile fractions removed in vacuo
8. 8
   その他to afford a crude tan solid
9. 9
   その他The crude solid was recrystallized from toluene (150 cm3)

実験手順

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.

出典