C(N(CC)CC)C.[OH:8][CH2:9][CH2:10][N:11]1[CH:15]=[C:14]([I:16])[CH:13]=[C:12]1[CH:17]=[O:18].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1.O>ClCCl>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([O:8][CH2:9][CH2:10][N:11]2[CH:15]=[C:14]([I:16])[CH:13]=[C:12]2[CH:17]=[O:18])(=[O:28])=[O:27])=[CH:22][CH:21]=1Triethylamine (3.3 mL, 23.8 mmol) was added to a stirred solution of 1-(2-hydroxyethyl)-4-iodo-pyrrole-2-carbaldehyde (2.1 g, 7.92 mmol) in dichloromethane (15 mL). The reaction mixture was chilled to 0° C. and 4-methyl-benzenesulfonyl chloride (1.82 g, 9.51 mmol) was added over 15 min. The reaction mixture was allowed to warm to ambient temperature and stirred overnight. Water was added, the organic phase separated and the aqueous phase extracted with dichloromethane. The combined organic layers were washed with saturated sodium bicarbonate solution, brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue which was purified by washing with petroleum ether to afford 2-(2-formyl-4-iodo-pyrrol-1-yl)ethyl 4-methylbenzenesulfonate (2.4 g, 72%) as a grey solid.
Wird geladen…
