Methyl iodide → HCID 66646915, compound

HRID 536706Notes

Reaction equation

HRID 536706 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:10][CH2:11][C@@H:12]2[C@@H:16]([OH:17])[CH2:15][CH2:14][O:13]2)=[CH:5][CH:4]=1.[H-].[Na+].I[CH3:35]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:10][CH2:11][C@@H:12]2[C@@H:16]([O:17][CH3:35])[CH2:15][CH2:14][O:13]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13845246HCID 13845246, compound

Product 1

HCID 66646915HCID 66646915, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 22C (620 mg, 1.47 mmol) in DMF (5 mL) was treated with NaH (60%)(88 mg, 2.2 mmol). The mixture was stirred for 10 min at rt. To the mixture was added dropwise iodomethane (251 mg, 1.57 mmol). The reaction was stirred at rt for 12 hrs. The reaction mixture was quenched with water and extracted with EtOAc. The organic was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford 574 mg (90%) of the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 1.91-2.02 (m, 2H) 3.09 (dd, J=9.82, 5.52 Hz, 1H) 3.15 (dd, J=9.82, 4.91 Hz, 1H) 3.31 (s, 3H) 3.78 (s, 6H) 3.81-3.93 (m, 2H) 3.94-4.06 (m, 2H) 6.77-6.87 (m, 4H) 7.16-7.23 (m, 1H) 7.26-7.37 (m, 6H) 7.40-7.48 (m, 2H).

Workup

  1. stirringThe reaction was stirred at rt for 12 hrs
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialThe organic was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-43c3f3c1994145909e51077b6b885a79
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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