HCID 241612, compound → HCID 13476441, compound

HRID 1981870Notes

Reaction equation

HRID 1981870 reaction equation
[C:1]([CH:9]=[CH:10][C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([OH:18])(=[S:17])[CH3:16]>C(OCC)C>[C:15]([S:17][CH:10]([CH2:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:18])[CH3:16]

Participants

4

Reactant 2

HCID 241612HCID 241612, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 13476441HCID 13476441, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.90 g of methyl 3-benzoylacrylate was dissolved in 30 ml of diethyl ether, and 0.8 ml of thioacetic acid was added thereto. The mixture was stirred for 5 hours at room temperature. 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 using a mixture of hexane and diethyl ether as an eluent, and then recrystallized from the same mixture to give 2.42 g of methyl 2-acetylthio-3-benzoylpropionate.

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
  5. additiona mixture of hexane and diethyl ether as an eluent
  6. customrecrystallized from the same mixture

Sources & evidence

ORD record
ord-08391010ad0b45479b52f0b2621adecc
Source dataset
uspto-grants-1986_06
Patent number
US04594197

Reaction notes

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