Dimethylformamide → HCID 22037436, compound

HRID 1167517Notes

Reaction equation

HRID 1167517 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-17e2002563f748c7b839e99f3e9a65fd
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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