Ethyl Thioglycolate → Ethyl 4-[(2-ethoxy-2-oxoethyl)thio]butanoate

HRID 595070

Reaction equation

HRID 595070 reaction equation
[Na].[SH:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[CH2:7]([O:6][C:4]([CH2:3][S:2][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:5])[CH3:8]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 18474Ethyl 4-chlorobutyrateHCID 5360545Sodium2×

Product 1

HCID 2778847Ethyl 4-[(2-ethoxy-2-oxoethyl)thio]butanoateYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium metal (4.3 g, 0.18 mol) was added cautiously in small portions to ethanol (150 mL). After the sodium completely dissolved, the mixture was cooled to 0° C. and ethyl 2-sulfanylacetate (21.9 g, 0.18 mol), was added. Ethyl 4-chlorobutanoate (27.4 g, 0.18 mol) was then added slowly and the resulting mixture stirred overnight at rt. The solid was filtered off, and then the filtrate concentrated under reduced pressure. The oil obtained was partitioned between water and ethyl acetate. The organic layer was collected, dried over anhydrous Na2SO4 and concentrated under vacuum to give the desired ethyl 4-((ethoxycarbonyl)methylthio)butanoate (40.2 g, 95%) as colorless oil. The crude material was used without further purification in the follow step.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe oil obtained
  4. customwas partitioned between water and ethyl acetate
  5. customThe organic layer was collected
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-38879612a4614b2f9eb66bbcecbe9b03
Source dataset
uspto-grants-2016_01
Patent number
US09242993B2

Linked notes

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