Diethyl Ether → 3-(4-Benzyloxyphenyl)-2-ethylsulfanyl propanoic acid methyl ester

HRID 987280Notes

Reaction equation

HRID 987280 reaction equation
[OH-].[K+].[CH2:3]([SH:5])[CH3:4].[CH3:6][O:7][C:8](=[O:26])[CH:9](Cl)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1.C(OCC)C>CO>[CH3:6][O:7][C:8](=[O:26])[CH:9]([S:5][CH2:3][CH3:4])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6343EthanethiolHCID 14797Potassium HydroxideHCID 10780869Methyl 3-(4-benzyloxyphenyl)-2-chloropropanoate

Product 1

HCID 541051323-(4-Benzyloxyphenyl)-2-ethylsulfanyl propanoic acid methyl esterYield 86.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (0.092 g; 1.64 mmole) was dissolved in methanol. Ethanethiol (0.133 g; 2.14 mmole) and 3-(4-benzyloxyphenyl)-2-chloropropanoic acid methyl ester (0.5 g; 1.64 mmole) were added. The reaction mixture was stirred at room temperature over night. Diethyl ether (15 ml) was added. The mixture was filtered and evaporated. The residue was purified by adding active charcoal in methanol. The mixture was stirred for 15 minutes and the active charcoal was filtered off. Evaporation of the solvent gave 0.47 g (86.7% yield) of 3-(4-benzyloxyphenyl)-2-ethylsulfanyl propanoic acid methyl ester.

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated
  3. customThe residue was purified
  4. additionby adding active charcoal in methanol
  5. stirringThe mixture was stirred for 15 minutes
  6. filtrationthe active charcoal was filtered off
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-1073b56c4a234ce49c366e5a32311bb0
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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