1-(1H-Imidazol-1-yl)ethanone → HCID 66891447, compound

HRID 253316Notes

Reaction equation

HRID 253316 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:16][CH2:17][CH2:18][O:19][CH3:20])[C:5]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[C:6]([CH2:8][C:9]#[N:10])[CH:7]=1.[H-].[Na+].[C:23](N1C=CN=C1)(=[O:25])[CH3:24]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([O:16][CH2:17][CH2:18][O:19][CH3:20])[C:5]([O:11][CH2:12][CH2:13][O:14][CH3:15])=[C:6]([CH:8]([C:23](=[O:25])[CH3:24])[C:9]#[N:10])[CH:7]=1

Participants

5

Reactant 3

HCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 24758Sodium hydrideHCID 66891426HCID 66891426, compound

Product 1

HCID 66891447HCID 66891447, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)acetonitrile (250 mg, 0.88 mmol) in tetrahydrofuran (2 mL) was added to a suspension of sodium hydride (40% oil dispersion, 70 mg, 1.8 mmol) in tetrahydrofuran (5 mL), followed by the addition of 1-acetylimidazole (145 mg, 1.3 mmol). After five minutes at room temperature, stirring was continued at 60° C. for 20 minutes. After cooling to room temperature, the reaction mixture was quenched with hydrochloric acid (1M, 20 mL) and extracted with ethyl acetate (3×20 mL). The combined extract was washed with water and brine (20 mL each), dried over sodium sulfate, filtered and concentrated to give the crude 2-(5-fluoro-2,3-bis{[2-(methyloxy)ethyl]oxy}phenyl)-3-oxobutanenitrile (0.26 g, 0.80 mmol, 91% yield). 1H NMR (400 MHz, CDCl3): 6.73-6.69 (m, 2H), 4.29-4.21 (m, 2H), 4.15-4.13 (m, 2H), 3.79-3.76 (m 2H), 3.62-3.57 (m, 2H), 3.44 (s, 3H), 3.41 (s, 3H), 2.26 (s, 3H); MS (EI) for C16H20FNO5: 326 (MH+).

Workup

  1. waitwas continued at 60° C. for 20 minutes
  2. customthe reaction mixture was quenched with hydrochloric acid (1M, 20 mL)
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. extractionThe combined extract
  5. washwas washed with water and brine (20 mL each)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-243093f9a39d49d0bbcf2f2e816bce1e
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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