Sodium hydride → HCID 58031619, compound

HRID 560868Notes

Reaction equation

HRID 560868 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[S:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[H-].[Na+].Br[CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C)C=O>[Si:24]([O:23][CH2:22][CH2:21][N:9]1[CH2:10][CH2:11][N:7]([C:5]2[S:4][C:3]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:2]([CH3:1])[CH:6]=2)[C:8]1=[O:12])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 58031554Ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate

Product 1

HCID 58031619HCID 58031619, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of ethyl 3-methyl-5-(2-oxoimidazolidin-1-yl)thiophene-2-carboxylate (0.85 g, 3.33 mmol) in anhydrous N,N-dimethylformamide (8 mL) under nitrogen atmosphere was added in one portion sodium hydride (60% in mineral oil, 0.16 g, 4.00 mmol). The resulting reaction mixture was stirred at ambient temperature for 1 h, and then (2-bromoethoxy)(tert-butyl)dimethylsilane (0.86 mL, 4.01 mmol) was added. The resulting reaction mixture was stirred at ambient temperature for 16 h, and then partitioned between ethyl acetate (100 mL), water (35 mL) and brine (35 mL). The aqueous layer was extracted with ethyl acetate (100 mL), and the combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with 0-30% ethyl acetate in hexanes to afford the title compound as a colorless solid in 79% yield (1.09 g): 1H NMR (300 MHz, CDCl3) δ 6.13 (s, 1H), 4.26 (q, J=7.1 Hz, 2H), 3.85-3.69 (m, 6H), 3.41 (t, J=5.2 Hz, 2H), 2.49 (s, 3H), 1.33 (t, J=7.1 Hz, 3H), 0.89 (s, 9H), 0.06 (s, 6H): MS (ES+) m/z 413.4 (M+1).

Workup

  1. customThe resulting reaction mixture
  2. customThe resulting reaction mixture
  3. stirringwas stirred at ambient temperature for 16 h
  4. custompartitioned between ethyl acetate (100 mL), water (35 mL) and brine (35 mL)
  5. extractionThe aqueous layer was extracted with ethyl acetate (100 mL)
  6. dry with materialthe combined organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography
  10. washeluted with 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1809d502f2aa4f27b833f51b5a791684
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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