Methyl iodide → HCID 22258075, compound

HRID 1611002Notes

Reaction equation

HRID 1611002 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:14][CH:13]=[CH:12][C:11]=1[CH:25]([OH:29])[C:26]([OH:28])=[O:27].[H-].[Na+].[CH3:32]I>COCCOC.[Cl-].[NH4+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][O:9][C:10]1[C:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])=[CH:14][CH:13]=[CH:12][C:11]=1[CH:25]([O:29][CH3:32])[C:26]([OH:28])=[O:27]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9932554HCID 9932554, compound

Product 1

HCID 22258075HCID 22258075, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a stirred solution of Example 1 Part B compound (112 mg, 0.243 mmol) in DME (1 mL) under argon at room temperature was added sodium hydride (60% mineral oil dispersion, 9.7 mg, 0.24 mmol). After 30 min, methyl iodide (15 μL, 0.24 mmol) was added, the reaction mixture was stirred for 18 h and then diluted with saturated ammonium chloride solution. The mixture was extracted three times with Et2O. The organic extracts were combined, washed once with water, once with brine, dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel provided the title compound as a colorless oil, 67 mg (58% yield). LC/MS gave the correct molecular ion [(M+H)+=475] for the desired compound.

Workup

  1. extractionThe mixture was extracted three times with Et2O
  2. washwashed once with water, once with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-211a87420d754c23a1c53f025f7398a7
Source dataset
uspto-grants-2006_01
Patent number
US06984645B2

Reaction notes

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