1-Iodohexane → 5-(Hexyloxy)-2-methyl-1H-indole-3-acetic acid

HRID 484256

Reaction equation

HRID 484256 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[CH2:12][C:13]([OH:15])=[O:14].C[O-].[Na+].[CH2:19](I)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>CO>[CH2:19]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[C:5]2[CH2:12][C:13]([OH:15])=[O:14])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 125271-IodohexaneHCID 10942334Sodium MethoxideHCID 11310252O-Desmethyl-N-deschlorobenzoyl Indomethacin

Product 1

HCID 199357575-(Hexyloxy)-2-methyl-1H-indole-3-acetic acidYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-hydroxy-2-methyl-1H-indole-3-acetic acid (7.17 g, 35.0 mmol) in methanol (40 mL) is added sodium methoxide (70 mmol). The solution is evaporated, dimethylformamide (40 mL) is added followed by hexyl iodide (35.0 mmol). After 2 days the solvent is removed and the residue is partitioned between ethyl acetate and pH=4 buffer. The organic layer is separated, dried over MgSO4 and evaporated to 8.6 g of a brown solid. Recrystallization from ethanol/water affords 6.23 g (62%) of white crystals, m.p. 65°-67° C.

Workup

  1. customThe solution is evaporated
  2. additiondimethylformamide (40 mL) is added
  3. customAfter 2 days the solvent is removed
  4. customthe residue is partitioned between ethyl acetate and pH=4 buffer
  5. customThe organic layer is separated
  6. dry with materialdried over MgSO4
  7. customevaporated to 8.6 g of a brown solid
  8. customRecrystallization from ethanol/water

Sources & evidence

ORD record
ord-1e2dbac9c99d4930a37317edb68511d2
Source dataset
uspto-grants-1993_07
Patent number
US05229516

Linked notes

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