Ethanol → 4-(2-Monomethoxytrityloxyethylthio)dihydrocinnamic acid

反応式

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

参加物

反応物 4

HCID 702Ethanol

HCID 81531Diisopropylethylamine

HCID 5797844-Mercaptohydrocinnamic Acid

HCID 230366832-Chloroethyl monomethoxytrityl ether

生成物 1

HCID 1317165144-(2-Monomethoxytrityloxyethylthio)dihydrocinnamic acid収率 80%

実験手順

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.