Methyl iodide → HCID 90919910, compound

HRID 1242813Notes

Reaction equation

HRID 1242813 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[CH2:8][C@@H:7]([CH2:9][OH:10])[N:6]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[O:12])[CH2:5]1.[H-].[Na+].[CH3:27]I>O1CCCC1>[CH3:1][O:2][N:3]=[C:4]1[CH2:8][C@@H:7]([CH2:9][O:10][CH3:27])[N:6]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)=[O:12])[CH2:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58585503HCID 58585503, compound

Product 1

HCID 90919910HCID 90919910, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of alcohol (2) (EZ mixture, 20 mg, 0.06 mmol) and sodium hydride (3 mg, 0.12 mmol) in tetrahydrofuran (1 ml) under argon, was added methyl iodide (7.7 μl, 0.12 mmol). The reaction mixture was stirred overnight and quenched with water. The mixture was diluted with ethyl acetate and washed with brine, dried (MgSO4) and concentrated in vacuo. The crude was purified on silica gel preparative chromatography using DCM: MeOH 100:0 then 95:5.

Workup

  1. customquenched with water
  2. additionThe mixture was diluted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified on silica gel preparative chromatography

Sources & evidence

ORD record
ord-0334253b6f464e2f9ea6e173e55ed7f1
Source dataset
uspto-grants-2006_10
Patent number
US07115754B2

Reaction notes

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