Sodium hydride → HCID 90387295, compound

HRID 2170232Notes

Reaction equation

HRID 2170232 reaction equation
[CH:1]([C:3]1[C:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:8])[NH:6][CH:7]=1)=[O:2].[H-].[Na+].Cl[CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22]>O1CCCC1>[CH:1]([C:3]1[C:4]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:8])[N:6]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:7]=1)=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 71371758Ethyl 4-formyl-2-methyl-1H-pyrrole-3-carboxylate

Product 1

HCID 90387295HCID 90387295, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 93b (8.826 g, 48.7 mmol) in tetrahydrofuran (325 mL) was chilled in an ice bath and treated with sodium hydride (dry, 95%) (2.454 g, 97 mmol) added portionwise over 15 minutes. The mixture was stirred under N2 for 10 minutes and treated with (2-(chloromethoxy)ethyl)trimethylsilane (12 mL, 67.8 mmol), then stirred for 50 minutes. The reaction vessel was removed from the ice bath and allowed to warm to ambient temperature. The reaction mixture was carefully quenched with 200 mL of saturated aqueous ammonium chloride, reduced in volume by rotovap and shaken in a separatory funnel with 350 mL each of ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous magnesium sulfate), filtered and concentrated. The crude material was chromatographed on a 330 g silica gel cartridge eluting with 0-50% ethyl acetate/heptane to provide the title compound.

Workup

  1. additionadded portionwise over 15 minutes
  2. stirringstirred for 50 minutes
  3. customThe reaction vessel was removed from the ice bath
  4. customThe reaction mixture was carefully quenched with 200 mL of saturated aqueous ammonium chloride
  5. stirringshaken in a separatory funnel with 350 mL each of ethyl acetate and water
  6. washThe organic layer was washed with saturated aqueous sodium chloride
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material was chromatographed on a 330 g silica gel cartridge
  11. washeluting with 0-50% ethyl acetate/heptane

Sources & evidence

ORD record
ord-924f1c8b7ec749659f45905dfa43c06d
Source dataset
uspto-grants-2015_06
Patent number
US09050346B2

Reaction notes

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