Butyl iodide → Methyl 1-butyl-1H-indole-5-carboxylate

HRID 348948

Reaction equation

HRID 348948 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CC(C)([O-])C.[K+].I[CH2:21][CH2:22][CH2:23][CH3:24]>CS(C)=O>[CH2:21]([N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 2737635methyl 1H-indole-5-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 21086133Methyl 1-butyl-1H-indole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of methyl 1H-indole-5-carboxylate (6.0 g) in methylsulfoxide (30 mL) was added potassium t-butoxide (3.88 g). The mixture was stirred at room temperature for 10 minutes at which time 1-iodobutane (1.8 mL) was added. The mixture was stirred at room temperature for 5 h then partitioned between water and methylene chloride. The layers were separated and the organic layer washed three times with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Column chromatography on silica gel (100 mL) using 10% ethyl acetate in hexanes as eluent to give 6.18 g of the title compound: 1H NMR (CDCl3) δ 0.923, 1.38, 1.83, 3.9, 4.14, 6.58, 7.15, 7.34, 7.9, 8.39.

Workup

  1. additionwas added
  2. customthen partitioned between water and methylene chloride
  3. customThe layers were separated
  4. washthe organic layer washed three times with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b8973057a0f4464ac282a0a483121b7
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

Loading…