반응 #1471076

반응 방정식

methyl 3-(4-hydroxyphenyl)propionate

N-methyl-N-dodecylethanolamine

triphenylphosphine

diisopropyl azodicarboxylate

→

3-{4-[2-(N-dodecyl-N-methylamino)ethoxy]phenyl} propanoic acid, methyl ester

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.ADDITIONadded dropwise over 50 min
2. 2
   기타the reaction mixture was evaporated under reduced pressure
3. 3
   기타the residue was triturated with hexane
4. 4
   기타The solid formed
5. 5
   여과was filtered
6. 6
   세척washed with hexane
7. 7
   기타the combined filtrate was chromatographed on silica gel using a gradient of ethyl acetate in hexane (20%-60%) as eluent
8. 8
   workup.DISTILLATIONDistillation under vacuum

실험 절차

A solution of methyl 3-(4-hydroxyphenyl)propionate (10.0 g, 55. 5 mmol), N-methyl-N-dodecylethanolamine (13.5 g, 55.5 mmol) and triphenylphosphine (16.0 g, 61.0 mmol) in dry tetrahydrofuran (200 ml) was treated at 22° C. with diisopropyl azodicarboxylate (12.3 g, 61.0 mmol) added dropwise over 50 min. After 3 h at 22° C., the reaction mixture was evaporated under reduced pressure and the residue was triturated with hexane. The solid formed was filtered, washed with hexane and the combined filtrate was chromatographed on silica gel using a gradient of ethyl acetate in hexane (20%-60%) as eluent. Distillation under vacuum then gave 18.0 g (75%) of 3-{4-[2-(N-dodecyl-N-methylamino)ethoxy]phenyl} propanoic acid, methyl ester as a clear oil: b.p. 180-183° C./0.02 torr (bulb to bulb distillation, air bath temperature).

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