HCID 178418630, compound → HCID 22350097, compound

HRID 896663Notes

Reaction equation

HRID 896663 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][SH:10](=S)=S)=[CH:5][CH:4]=1.[CH:13]1([Mg]Br)[CH2:15][CH2:14]1>C1COCC1.[Cl-].[NH4+].C(OCC)(=O)C>[CH:13]1([S:10][CH2:9][C:6]2[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)[CH2:15][CH2:14]1

Participants

6

Reactant 2

HCID 178418630HCID 178418630, compoundHCID 178503238HCID 178503238, compound

Product 1

HCID 22350097HCID 22350097, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
21 °C

Procedure

To a solution of (4-methylsulfanyl-phenyl)-methanethiol disulfide from Step 1 in THF (50 mL) at 21° C. was added cyclopropylmagnesium bromide (excess) dropwise. The reaction mixture was stirred 18 h at 21° C., then diluted with a saturated ammonium chloride solution and ethyl acetate. The organic extracts were washed (H2O), (brine), dried (MgSO4), filtered and concentrated. Purification by flash chromatography (eluting with hexane/ethyl acetate, 98:2) provided the 1-cyclopropylsulfanylmethyl-4-methylsulfanyl-benzene compound as an oil.

Workup

  1. washThe organic extracts were washed (H2O), (brine),
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification
  6. washby flash chromatography (eluting with hexane/ethyl acetate, 98:2)

Sources & evidence

ORD record
ord-395fc63e04e541eb8199fdf131dd5962
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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