Ethanol → 4-(2-Monomethoxytrityloxyethylthio)dihydrocinnamic acid

HRID 1709741Notes

Reaction equation

HRID 1709741 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

5

Reactant 4

HCID 702EthanolHCID 81531DiisopropylethylamineHCID 5797844-Mercaptohydrocinnamic AcidHCID 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.

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 12 hours
  3. customThe solvent was removed by distillation under a reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8fb8cd789d25458bae5ef8117354cf3b
Source dataset
uspto-grants-1990_08
Patent number
US04950745

Reaction notes

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