2-(Trimethylsilyl)ethanethiol → 2-Cyano-4-(3-furyl)-7-mercaptonaphthalene

HRID 1901132Notes

Reaction equation

HRID 1901132 reaction equation
[C:1]([C:3]1[CH:12]=[C:11]([C:13]2[CH:17]=[CH:16][O:15][CH:14]=2)[C:10]2[C:5](=[CH:6][C:7](I)=[CH:8][CH:9]=2)[CH:4]=1)#[N:2].C[Si](C)(C)CC[SH:23].CC(C)([O-])C.[K+]>CCO>[C:1]([C:3]1[CH:12]=[C:11]([C:13]2[CH:17]=[CH:16][O:15][CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]([SH:23])=[CH:8][CH:9]=2)[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 2055212-(Trimethylsilyl)ethanethiolHCID 233702222-Cyano-4-(3-furyl)-7-iodonaphthaleneHCID 23665647Potassium tert-butoxide

Product 1

HCID 233702312-Cyano-4-(3-furyl)-7-mercaptonaphthalene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-cyano-4-(3-furyl)-7-iodonaphthalene (1 g), 2-(trimethylsilyl)ethane thiol (390 mg), potassium tert-butoxide (650 mg) and tetrakis (triphenylphosphine)palladium (100 mg) in EtOH (5 mL) was reluxed for 90 min. The solvent was evaporated and the residue partitioned between Et2O and H2O. The organic phase was dried (MgSO4) and concentrated and the residue was dissolved in DMF (24 mL). To this solution was added Bu4NF (7.7 mL of a 1M THF solution). After 30 min., 1N HCl was added followed by H2O. The precipitate that formed was filtered and washed with H2O to provide the title compound as a solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between Et2O and H2O
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. dissolutionthe residue was dissolved in DMF (24 mL)
  6. additionTo this solution was added Bu4NF (7.7 mL of a 1M THF solution)
  7. waitAfter 30 min.
  8. addition1N HCl was added
  9. customThe precipitate that formed
  10. filtrationwas filtered
  11. washwashed with H2O

Sources & evidence

ORD record
ord-2f2cd4ad1aa04a3d803ed9731b027dab
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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