Ethanol → 4-(2-Monomethoxytrityloxyethylthio)dihydrocinnamic acid

Reaction equation

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

Participants

Reactant 4

HCID 702Ethanol

HCID 81531Diisopropylethylamine

HCID 5797844-Mercaptohydrocinnamic Acid

HCID 230366832-Chloroethyl monomethoxytrityl ether

Product 1

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

Procedure

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.