HCID 53748468, compound → HCID 20266263, compound

HRID 1719664Notes

Reaction equation

HRID 1719664 reaction equation
[C:1]1([C:7]2[CH:20]=[CH:19][C:10]([C:11]([CH:13]=[CH:14][C:15]([O:17][CH3:18])=[O:16])=[S:12])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21]([OH:24])(=[S:23])[CH3:22]>C(OCC)C>[C:21]([S:23][CH:14]([CH2:13][C:11](=[S:12])[C:10]1[CH:19]=[CH:20][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][CH:9]=1)[C:15]([O:17][CH3:18])=[O:16])(=[O:24])[CH3:22]

Participants

4

Reactant 2

HCID 53748468HCID 53748468, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 20266263HCID 20266263, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2.98 g of methyl 3-(4-phenylthiobenzoyl)acrylate in 30 ml of diethyl ether was added 0.8 ml of thioacetic acid, and the resulting mixture was stirred at room temperature for 5 hours. The reaction solution was washed, in turn, with water, a saturated aqueous solution of sodium hydrogencarbonate and water, and dried over magnesium sulfate. The diethyl ether was removed from the solution by evaporation, and the residue was purified by silica gel column chromatography (eluent: hexane-diethyl ether) to give 3.73 g of methyl 2-acetylthio-3-(4-phenylthiobenzoyl)propionate as an oil.

Workup

  1. washThe reaction solution was washed, in turn, with water
  2. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water, and dried over magnesium sulfate
  3. customThe diethyl ether was removed from the solution by evaporation
  4. customthe residue was purified by silica gel column chromatography (eluent: hexane-diethyl ether)

Sources & evidence

ORD record
ord-676c9d0b12054f0e9b87657c043697a3
Source dataset
uspto-grants-1985_09
Patent number
US04541959

Reaction notes

Loading…