Methyl iodide → HCID 14676889, compound

HRID 1165582Notes

Reaction equation

HRID 1165582 reaction equation
[CH:1]([CH:3]1[C:8]2[N:9]([CH3:16])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:7]=2[S:6][CH2:5][CH2:4]1)=[O:2].[H-].[Na+].[CH3:19]I>O1CCCC1>[CH:1]([C:3]1([CH3:19])[C:8]2[N:9]([CH3:16])[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:7]=2[S:6][CH2:5][CH2:4]1)=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14676867HCID 14676867, compound

Product 1

HCID 14676889HCID 14676889, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-formyl-5-methyl-2,3,4,5-tetrahydrothiopyrano[3,2-b]indole (2.31 g) in dry tetrahydrofuran (25 ml) is mixed with 50% sodium hydride (480 mg) and stirred at room temperature for 1.5 hours. Under ice cooling, a solution of methyl iodide (1.7 g) in dry tetrahydrofuran (5 ml) is added dropwise thereto over 5 minutes. The mixture is stirred further for 1.5 hours at room temperature and poured into ice water, which is extracted with ether. The extract is washed with water, dried and evaporated to dryness. The residue is applied to liquid chromatography eluted with benzene/hexane (5:1) to give the title compound (1.62 g): Yield 66.2%.

Workup

  1. waitover 5 minutes
  2. stirringThe mixture is stirred further for 1.5 hours at room temperature
  3. extractionis extracted with ether
  4. washThe extract is washed with water
  5. customdried
  6. customevaporated to dryness
  7. washeluted with benzene/hexane (5:1)

Sources & evidence

ORD record
ord-073dbac6da8e4da3a9175e753e1fc55c
Source dataset
uspto-grants-1990_03
Patent number
US04910318

Reaction notes

Loading…