تفاعل #78259

معادلة التفاعل

(7aS,6R)-2-(3,5-dichloro-phenyl)-6-hydroxy-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione

Ph3P

4-bromophenol

DIAD

→

titled compound

المردود 6.6%

(7aS,6S)-2-(3,5-dichloro-phenyl)-6-(4-bromophenoxy)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione

المردود 6.6%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter evaporating the solvent
2. 2
   workup.DISSOLUTIONthe residue was dissolved in DCM
3. 3
   غسيلwashed with NaHCO3 solution, water
4. 4
   تجفيفdried over MgSO4
5. 5
   أخرىthe solvent was evaporated under reduced pressure

الإجراء التجريبي

To a solution of (7aS,6R)-2-(3,5-dichloro-phenyl)-6-hydroxy-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione (0.5 g) (1.67 mmol) (Preparation 2), Ph3P (0.44 g) (1eq.) and 4-bromophenol (0.29 g) (1 eq.) in 5 mL of dry THF at 0° C. was added DIAD (0.337 g) in a minimal volume of THF. The reaction mixture was warmed to RT overnight. After evaporating the solvent, the residue was dissolved in DCM, washed with NaHCO3 solution, water, dried over MgSO4, and the solvent was evaporated under reduced pressure, to afford after SiO2 chromatography (eluent: DCM) the titled compound as a white solid (50 mg). Mp=116° C. NMR (DMSO, 200 MHz): 7.75 (1H, m), 7.5-7.4 (4H, d+d), 6.85 (2H, d), 5.1 (1H, m), 4.6 (1H, dd), 3.95 (1H, dd), 3.35 (1H, dd), 2.7-2.5 (1H, m), 2.25 (1H, bd).

المصدر