Ethanol → 4-(2-Monomethoxytrityloxyethylthio)dihydrocinnamic acid

반응식

CO[C:3]1[CH:25]=[CH:24][CH:23]=[CH:22][C:4]=1[C:5]([O:18][CH2:19][CH2:20]Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[SH:26][C:27]1[CH:37]=[CH:36][C:30]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:29][CH:28]=1.C(N(C(C)C)CC)(C)C.[CH2:47]([OH:49])C>>[CH3:47][O:49][CH:19]([O:18][C:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:4]1[CH:3]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:20][S:26][C:27]1[CH:28]=[CH:29][C:30]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:36][CH:37]=1

참가 물질

반응물 4

HCID 702Ethanol

HCID 81531Diisopropylethylamine

HCID 5797844-Mercaptohydrocinnamic Acid

HCID 230366832-Chloroethyl monomethoxytrityl ether

생성물 1

HCID 1317165144-(2-Monomethoxytrityloxyethylthio)dihydrocinnamic acid수율 80%

실험 절차

2-Chloroethyl monomethoxytrityl ether <1> (2.1172 g, 6 mmol) and 4-mercaptodihydrocinnamic acid <2> (0.9112 g, 5 mmol) were dissolved in ethanol (15 ml), and diisopropylethylamine (2.45 ml, 15 mmol) was added to the solution and the mixture was heated and refluxed for 12 hours. The solvent was removed by distillation under a reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1.9945 g (yield=80%) of 4-(2-monomethoxytrityloxyethylthio)dihydrocinnamic acid <3> in the form of a syrup.