Sodium → 3-methoxy-4-thioacetoxy-2E-butenoic acid methyl ester
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
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 '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 chloride for precipitation of the remaining salt. After 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
- filtrationThe precipitated salt is filtered off
- customthe solvent is evaporated on the rotary evaporator
- additionmixed with a little methylene chloride for precipitation of the remaining salt
- filtrationAfter filtering off
- customevaporation of the solvent
- dry with materialdrying of the residue in a high vacuum, 36.53 g of a yellow-colored liquid with a content
- customis obtained
Sources & evidence
- ORD record
- ord-95d8a26777ef403189bae94816f29219
- Source dataset
- uspto-grants-1990_06
- Patent number
- US04931570
Reaction notes
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