Sodium hydride → HCID 21027709, compound

HRID 1827957Notes

Reaction equation

HRID 1827957 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:6][N:5]=1.Br[CH2:15][CH2:16][O:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][O:19]1.[I-].[Li+]>O1CCCC1.C(OCC)(=O)C.O>[CH2:12]([O:11][C:9]([C:7]1[CH:8]=[C:4]([CH3:3])[N:5]([CH2:15][CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[N:6]=1)=[O:10])[CH3:13]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 66321Lithium iodideHCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 178469061HCID 178469061, compound

Product 1

HCID 21027709HCID 21027709, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of sodium hydride (934 mg, 23.4 mmol) in tetrahydrofuran (50 mL) was treated with ethyl 3-methylpyrazole-5-carboxylate (3.00 g, 19.5 mmol) and the reaction mixture stirred at room temperature for 30 minutes. 2-(2-Bromoethoxy)tetrahydro-2H-pyran (3.5 mL, 19.5 mmol) and lithium iodide (50 mg, 0.39 mmol) were added and the reaction mixture refluxed for 16 hours. The reaction mixture was cooled and taken up in ethyl acetate and water. The organics were separated and washed with 10% citric acid solution, water, saturated sodium hydrogencarbonate solution and brine, dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol 99:1 to 95:5 to yield the title product, 4.47 g.

Workup

  1. temperaturethe reaction mixture refluxed for 16 hours
  2. temperatureThe reaction mixture was cooled
  3. customThe organics were separated
  4. washwashed with 10% citric acid solution, water, saturated sodium hydrogencarbonate solution and brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol 99:1 to 95:5

Sources & evidence

ORD record
ord-f2fa14885c7f43b0a23a6fe69d635896
Source dataset
uspto-grants-2006_06
Patent number
US07056934B2

Reaction notes

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