Methyl iodide → HCID 57742132, compound

HRID 660321Notes

Reaction equation

HRID 660321 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][O:14][CH3:15])[CH:7]=1)[CH3:2].[H-].[Na+].I[CH3:20]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][O:14][CH3:15])[CH:7]=1)[CH3:20])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57742154HCID 57742154, compound

Product 1

HCID 57742132HCID 57742132, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (3-Methoxymethoxy-phenyl)-acetic acid ethyl ester (31.2 g) in DMF (200 mL) was slowly added sodium hydride (6.21 g) and iodomethane (22.3 g) at 0°. After stirred for 20 h at 0°, this reaction mixture was quenched with water. This mixture was extracted with EtOAc, and combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=10:1) to afford the product as colorless oil.

Workup

  1. customat 0°
  2. customthis reaction mixture was quenched with water
  3. extractionThis mixture was extracted with EtOAc
  4. dry with materialwas dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was chromatographed on silica gel (n-Hex:EtOAc=10:1)

Sources & evidence

ORD record
ord-7e16d92d5dfd4d97a3f2dd8ed40c00ae
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

Loading…