Dimethylformamide → HCID 22037436, compound

HRID 2230337Notes

Reaction equation

HRID 2230337 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])N=[CH:4]1.[CH3:12][Si:13]([CH2:16][CH2:17][O:18][CH2:19]Cl)([CH3:15])[CH3:14].[CH3:21]N(C=O)C>>[CH3:12][Si:13]([CH3:15])([CH3:14])[CH2:16][CH2:17][O:18][CH2:19][N:3]1[CH:4]=[CH:21][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:7]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178418785HCID 178418785, compound

Product 1

HCID 22037436HCID 22037436, compound

Procedure

To a suspension of sodium hydride (1.0 g, 0.025 mol) in 50 mL of DMF was added methyl 4-imidazolecarboxylate (2.95 g, 0.023 mol) portionwise at room temperature. The mixture was stirred at room temperature for 0.5 hours. Then SEM-Cl (4.17 g, 0.025 mol) was added dropwise over 5 minutes. The reaction mixture was stirred for 4 hours and quenched by adding water. The aqueous phase was extracted with ethyl acetate and the organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and the crude was purified by chromatography on silica gel (ethyl acetate/hexane, 8:2) to give 4.0 g of the major regioisomer as a clear oil.

Workup

  1. stirringThe reaction mixture was stirred for 4 hours
  2. customquenched
  3. additionby adding water
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe crude was purified by chromatography on silica gel (ethyl acetate/hexane, 8:2)
  10. customto give 4.0 g of the major regioisomer as a clear oil

Sources & evidence

ORD record
ord-82f4ec8181f9461babf559a0d98df280
Source dataset
uspto-grants-2002_07
Patent number
US06423713B1

Reaction notes

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