Probucol → {2,6-Di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-1-methyl-ethylsulfanyl]-phenoxy}-acetic acid ethyl ester

HRID 916987

Reaction equation

HRID 916987 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][C:17]([S:20][C:21]2[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:24]([OH:31])=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:22]=2)([CH3:19])[CH3:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].I[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].[F-].[K+]>CN(C)C=O.CCOCC>[CH2:41]([O:40][C:38](=[O:39])[CH2:37][O:11][C:10]1[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:8][C:7]([S:16][C:17]([S:20][C:21]2[CH:22]=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:24]([OH:31])=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:26]=2)([CH3:18])[CH3:19])=[CH:6][C:5]=1[C:2]([CH3:1])([CH3:3])[CH3:4])[CH3:42]

Participants

6

Reactant 3

HCID 4912ProbucolHCID 12183Ethyl iodoacetateHCID 522689Potassium Fluoride

Product 1

HCID 11157727{2,6-Di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-1-methyl-ethylsulfanyl]-phenoxy}-acetic acid ethyl esterYield 27.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of probucol (0.5 g, 0.97 mmol) in dimethylformamide (1.5 mL) were added ethyl iodoacetate (0.31 g, 1.45 mmol) and 40% potassium fluoride on alumina (0.7 g, 4.8 mmol). The mixture was stirred for 24 hours and then diluted with ether (25 mL), filtered and washed with water (2×5 mL). The ether layer was dried over MgSO4, filtered and concentrated. Silica gel chromatography (hexanes/ether 5:95) yielded 160 mg of {2,6-di-tert-butyl-4-[1-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-1-methyl-ethylsulfanyl]-phenoxy}-acetic acid ethyl ester which was used directly for the next step of reaction.

Workup

  1. filtrationfiltered
  2. washwashed with water (2×5 mL)
  3. dry with materialThe ether layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b15f5d83112436083226b23dd62dec0
Source dataset
uspto-grants-2007_09
Patent number
US07271274B2

Linked notes

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