Methyl iodide → HCID 15516432, compound

HRID 564842Notes

Reaction equation

HRID 564842 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([I:19])[C:9]=1[O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[CH2:5][OH:6].[H-].[Na+].[CH3:22]I.[NH4+].[Cl-]>C1COCC1>[CH3:22][O:6][CH2:5][C:4]1[CH:3]=[C:2]([I:1])[C:9]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[C:8]([I:19])[CH:7]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10719578HCID 10719578, compound

Product 1

HCID 15516432HCID 15516432, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3,5-diiodo-4-(4′-methoxyphenoxy)benzyl alcohol (9) (347 mg; 0.72 mmol) in dry THF under argon was cooled to 0° C. and treated with 60% sodium hydride in mineral oil (28 mg; 0.7 mmol). The reaction was stirred at 0° C. for 10 min, then allowed to warm to RT and stirred an additional 30 min. Methyl iodide (0.5 ml; 8.1 mmol) was added and the mixture stirred at RT for 18 h. The reaction was poured into saturated NH4Cl (20 ml) and extracted with EtOAc (20 ml). The organic layer was washed with saturated NaCl, dried over Drierite, and evaporated to a tan oil which solidified upon standing. The solid was dissolved in a minimum amount of CH2Cl2 (3 ml), applied to a silica gel column (30 g, 230-400 mesh) and eluted with EtOAc/hexanes (3:17). Product-containing fractions were combined and evaporated to give 231 mg of 3,5-diiodo-4-(4′-methoxyphenoxy)benzyl methyl ether (10) as a white solid. NMR (CDCl3) d 3.41 (s, 3H), 3.76 (s, 3H), 6.70 (m, 2H), 6.81 (m, 2H), 7.80 (s, 2H). TLC: Rf0.69 (EtOAc/hexanes, 3:7)

Workup

  1. temperatureto warm to RT
  2. stirringstirred an additional 30 min
  3. stirringthe mixture stirred at RT for 18 h
  4. extractionextracted with EtOAc (20 ml)
  5. washThe organic layer was washed with saturated NaCl
  6. dry with materialdried over Drierite
  7. customevaporated to a tan oil which
  8. dissolutionThe solid was dissolved in a minimum amount of CH2Cl2 (3 ml)
  9. washeluted with EtOAc/hexanes (3:17)
  10. customevaporated

Sources & evidence

ORD record
ord-708f42a5d480430ba9e678db633fa75b
Source dataset
uspto-grants-2001_01
Patent number
US06169104A

Reaction notes

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