Dimethyl Disulfide → HCID 19759362, compound

HRID 1586810Notes

Reaction equation

HRID 1586810 reaction equation
Br[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:9][CH:8]=2)[C:5]([C:32]#[N:33])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:39][S:40]SC>>[Si:15]([O:14][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([N:6]2[C:2]([S:40][CH3:39])=[CH:3][CH:4]=[C:5]2[C:32]#[N:33])=[CH:12][CH:11]=1)([C:28]([CH3:29])([CH3:30])[CH3:31])([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 12232Dimethyl DisulfideHCID 19759533HCID 19759533, compoundHCID 178418339Butyllithium

Product 1

HCID 19759362HCID 19759362, compound

Procedure

To a mixture of N,N,N'-N'-tetramethylethylenediamine (1.55 ml) and 5-bromo-1-(4-tert-butyldiphenylsilyloxymethylphenyl)pyrrole-2-carbonitrile (3.80 g) was added dropwise n-butyllithium solution (1.6M solution in n-hexane, 5.2 ml) during a period of 20 minutes at -60° C. under nitrogen atmosphere. The mixture was stirred for one hour at the same temperature and then dimethyldisulfide (1 ml) was added therein in one portion. The reaction mixture was allowed to warm to ambient temperature, stirred overnight at the same temperature and then poured into ice water. The separated oil was extracted with ethyl acetate. The organic layer was washed with water, dried, and concentrated in vacuo to give the residue, which was purified by column chromatography on silica gel to yield 1-(4-tert-butyldiphenylsilyloxymethylphenyl)-5-methylthiopyrrole-2-carbonitrile (1.94 g) as a solid.

Workup

  1. stirringstirred overnight at the same temperature
  2. extractionThe separated oil was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customto give the residue, which
  7. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9f0ab66322c946c7803715c49d637132
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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