Tetrahydrofuran → HCID 67939153, compound

HRID 981713Notes

Reaction equation

HRID 981713 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[CH:7][N:6]=1.O1CCCC1.Cl[CH2:23][O:24][CH2:25][CH2:26][O:27][CH3:28]>CCOCC>[CH3:23][O:24][CH2:25][CH2:26][O:27][CH2:28][N:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[N:6][CH:7]=1)[C:12]([CH:14]1[CH2:16][CH2:15]1)=[O:13]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 86308N-(6-methoxypyridin-3-yl)cyclopropanecarboxamide

Product 1

HCID 67939153HCID 67939153, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium hydride (0.33 g, 0.014 mol) and N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide (92.5 g, 0.014 mol) were added to dry tetrahydrofuran (THF). This mixture was stirred under N2 for one hour when methoxyethyl chloromethyl ether (1.6 g, 0.014 mol) was added dropwise to the stirred mixture. The reaction was stirred overnight and diluted with ether and washed with water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo nto give 2.4 g of a yellow oil of the title compound. The structure was confirmed by mass spectroscopy (MS), IR and NMR analysis.

Workup

  1. additionwas added dropwise to the stirred mixture
  2. washwashed with water
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-757104f4aa6143688efd53fd92a477f1
Source dataset
uspto-grants-1991_02
Patent number
US04992503

Reaction notes

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