Sodium → 3-methoxy-4-thioacetoxy-2E-butenoic acid methyl ester

HRID 1165083

Reaction equation

HRID 1165083 reaction equation
[Na].[C:2]([OH:5])(=[S:4])[CH3:3].[CH3:6][O:7][C:8](=[O:15])/[CH:9]=[C:10](/[O:13][CH3:14])\[CH2:11]Cl>CO>[CH3:6][O:7][C:8](=[O:15])/[CH:9]=[C:10](/[O:13][CH3:14])\[CH2:11][O:5][C:2](=[S:4])[CH3:3]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 6364655Methyl (E)-4-Chloro-3-methoxy-2-butenoateHCID 178418634HCID 178418634, compound

Product 1

HCID 1317163333-methoxy-4-thioacetoxy-2E-butenoic acid methyl esterYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

4.07 g (0.177 mol) of sodium is dissolved in 180 ml of methanol and cooled to 0° C. 13.47 g (0.171 mol) of thioacetic acid is instilled in this solution. Then this solution is mixed at 0° C. with a solution of 29.15 g (0.150 mol) of 3-methoxy-4-chloro-2E-butenoic acid methyl ester in 40 ml of methanol. It is stirred again overnight at room temperature. The precipitated salt is filtered off, the solvent is evaporated on the rotary evaporator and mixed with a little methylene filtering off, evaporation of the solvent and drying of the residue in a high vacuum, 36.53 g of a yellow-colored liquid with a content according to GC of 82.8 percent is obtained. This corresponds to 30.25 g of 100 percent product=98.7 percent yield. Further data concerning the compound is:

Workup

  1. filtrationThe precipitated salt is filtered off
  2. customthe solvent is evaporated on the rotary evaporator
  3. additionmixed with a little methylene filtering off,
  4. customevaporation of the solvent
  5. dry with materialdrying of the residue in a high vacuum, 36.53 g of a yellow-colored liquid with a content
  6. customis obtained

Sources & evidence

ORD record
ord-07bd276e3fe0492fbd6f12c5a5889d40
Source dataset
uspto-grants-1990_03
Patent number
US04906765

Linked notes

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