Dimethylformamide → HCID 22037436, compound

HRID 861040Notes

Reaction equation

HRID 861040 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-d6bb5487779b43009051efbb190b25b0
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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