Methyl 4-oxo-4-(4-phenoxyphenyl)but-2-enoate → HCID 13276507, compound

HRID 2418151Notes

Reaction equation

HRID 2418151 reaction equation
[O:1]([C:8]1[CH:21]=[CH:20][C:11]([C:12]([CH:14]=[CH:15][C:16]([O:18][CH3:19])=[O:17])=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([OH:25])(=[S:24])[CH3:23]>C(OCC)C>[C:22]([S:24][CH:15]([CH2:14][C:12](=[O:13])[C:11]1[CH:20]=[CH:21][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][CH:10]=1)[C:16]([O:18][CH3:19])=[O:17])(=[O:25])[CH3:23]

Participants

4

Reactant 2

HCID 53908224Methyl 4-oxo-4-(4-phenoxyphenyl)but-2-enoateHCID 178418634HCID 178418634, compound

Product 1

HCID 13276507HCID 13276507, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.82 g of methyl 3-(4-phenoxybenzoyl)acrylate were dissolved in 30 ml of diethyl ether, then 1.5 ml of thioacetic acid were added. The mixture was stirred for 3 hours. The reaction mixture was washed, in turn, with water, a saturated aqueous solution of sodium hydrogencarbonate and water and then dried over magnesium sulfate. The diethyl ether was removed by distillation under reduced pressure. The residue was purified first by silica gel column chromatography, eluted with a mixture of hexane and diethyl ether, then by recrystallization from a mixture of hexane and diethyl ether to give 2.91 g of methyl 2-acetylthio-3-(4-phenoxybenzoyl)-propionate.

Workup

  1. washThe reaction mixture was washed, in turn, with water
  2. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and water and then dried over magnesium sulfate
  3. customThe diethyl ether was removed by distillation under reduced pressure
  4. customThe residue was purified first by silica gel column chromatography
  5. washeluted with a mixture of hexane and diethyl ether
  6. customby recrystallization
  7. additionfrom a mixture of hexane and diethyl ether

Sources & evidence

ORD record
ord-5b703ee12b9a4357846b23280ce89c7a
Source dataset
uspto-grants-1984_09
Patent number
US04472316

Reaction notes

Loading…