Methyl iodide → HCID 18945162, compound

HRID 399826Notes

Reaction equation

HRID 399826 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].I[CH3:19]>C(Cl)(Cl)Cl.[Ag-]=O>[CH3:19][O:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[C:11]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 18945167HCID 18945167, compound

Product 1

HCID 18945162HCID 18945162, compound

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 3-hydroxymethyl-5-(pyrrol-1-yl)benzoate (2.0 g) in chloroform (30 ml) was added silver(I) oxide (8.0 g) and iodomethane (4.3 ml). The reaction mixture was stirred at 50° C. for 4.5 hours. After being cooled to room temperature, the slurry was filtered and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (10:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to afford methyl 3-methoxymethyl-5-(pyrrol-1-yl)benzoate (1.72 g)) as an oil.

Workup

  1. temperatureAfter being cooled to room temperature
  2. filtrationthe slurry was filtered
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (10:1)
  5. additionThe eluted fractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-bd68e95762104c75ac6e7228b5c4ac65
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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