Methyl (methylsulfinyl)methyl sulfide → 4-Tert-butyl-2-[5-{2-[2-methylsulfinyl-2-methylthioethenyl)phenylmethoxy}benzofuran-2-yl]thiazole

HRID 487706Notes

Reaction equation

HRID 487706 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH:27]=O)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][S:30]([CH2:32][S:33][CH3:34])=[O:31]>O1CCCC1>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[CH:27]=[C:32]([S:30]([CH3:29])=[O:31])[S:33][CH3:34])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 190926964-Tert-butyl-2-[5-(2-formylphenylmethoxy)benzofuran-2-yl]thiazole

Product 1

HCID 734745674-Tert-butyl-2-[5-{2-[2-methylsulfinyl-2-methylthioethenyl)phenylmethoxy}benzofuran-2-yl]thiazoleYield 32.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-tert-butyl-2-[5-(2-formylphenylmethoxy)benzofuran-2-yl]thiazole (0.61 g), methyl methylsulfinylmethyl sulfide (0.46 g) and triton B (phase transfer) (0.7 g) in tetrahydrofuran (3 ml) was stirred under reflux for 5 hours. After being cooled, the resulting mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with diluted aqueous hydrochloric acid and brine, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and chloroform (1:5). The fractions containing object compound were combined and concentrated in reduced pressure to give a syrup of 4-tert-butyl-2-[5-{2-[2-methylsulfinyl-2-methylthioethenyl)phenylmethoxy}benzofuran-2-yl]thiazole (0.25 g).

Workup

  1. temperatureunder reflux for 5 hours
  2. temperatureAfter being cooled
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with diluted aqueous hydrochloric acid and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a syrup
  8. washeluted with a mixture of ethyl acetate and chloroform (1:5)
  9. additionThe fractions containing object compound
  10. concentrationconcentrated in reduced pressure

Sources & evidence

ORD record
ord-5a0fbfef2cb04855bad7e2d2e793b957
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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