Iodine → Ethyl 2-{4-[hydroxy(2-oxothiolan-3-yl)methyl]phenyl}propionate

HRID 1685813Notes

Reaction equation

HRID 1685813 reaction equation
Br[CH:2]1[CH2:6][CH2:5][S:4][C:3]1=[O:7].[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:12][CH:11]=1)=[O:9].II>O1CCCC1.[Zn]>[OH:9][CH:8]([CH:2]1[CH2:6][CH2:5][S:4][C:3]1=[O:7])[C:10]1[CH:11]=[CH:12][C:13]([CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 807IodineHCID 127428403-Bromothiolan-2-oneHCID 13066570rac 2-(4-Formylphenyl)propionic Acid Ethyl Ester

Product 1

HCID 59202209Ethyl 2-{4-[hydroxy(2-oxothiolan-3-yl)methyl]phenyl}propionateYield 23.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-Bromothiolan-2-one (315 mg) and ethyl 2-(4-formylphenyl)propionate (300 mg) were dissolved in tetrahydrofuran, and to the solution was added zinc (147 mg) and a catalytic amount of iodine, and the reaction mixture was heated until the mixture was refluxed. The reaction mixture was stirred overnight at room temperature, then the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (106 mg, 20%).

Workup

  1. temperaturewas refluxed
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-bef886875c0241d4bfe00165b1b226a0
Source dataset
uspto-grants-2012_04
Patent number
US08148421B2

Reaction notes

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