Water → HCID 18784863, compound

HRID 1108300Notes

Reaction equation

HRID 1108300 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[C:16]2[O:15][CH:14]=[CH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.[CH3:17][S:18]SC.O>O1CCCC1>[CH3:6][O:7][C:8]1[C:16]2[O:15][C:14]([S:18][CH3:17])=[CH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 12232Dimethyl DisulfideHCID 5904627-MethoxybenzofuranHCID 178418339Butyllithium

Product 1

HCID 18784863HCID 18784863, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (1.6M in hexanes, 10.2 ml) was added dropwise to a cooled (-78° C.) solution of 7-methoxybenzofuran (2.0 g) in tetrahydrofuran (40 ml) under an inert atmosphere. Methyl disulfide (1.46 ml) was added and the reaction mixture was stirred at -78° C. for 30 minutes, then at room temperature for 1 h. Water was added and the tetrahydrofuran was removed in vacuo. The aqueous residue was extracted with ether (3×100 ml) and the combined organic phases were washed with water (100 ml) and dried over sodium sulfate. The solvent was removed in vacuo to afford the title compound as a yellow oil (2.73 g).

Workup

  1. waitat room temperature for 1 h
  2. customthe tetrahydrofuran was removed in vacuo
  3. extractionThe aqueous residue was extracted with ether (3×100 ml)
  4. washthe combined organic phases were washed with water (100 ml)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fd8987c04fe5459ba5c0f7caf6f6694c
Source dataset
uspto-grants-2000_05
Patent number
US06066657

Reaction notes

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