Tetrahydrofuran → HCID 20070560, compound

HRID 981714Notes

Reaction equation

HRID 981714 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.ClC[CH2:19][C:20]([CH3:25])([CH3:24])[C:21]([O-:23])=[O:22].O1CCC[CH2:27]1>CCOCC>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:27][O:23][C:21](=[O:22])[C:20]([CH3:25])([CH3:24])[CH3:19])[C:12]([CH:14]2[CH2:16][CH2:15]2)=[O:13])=[CH:7][N:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86308N-(6-methoxypyridin-3-yl)cyclopropanecarboxamideHCID 217530474-Chloro-2,2-dimethylbutanoate

Product 1

HCID 20070560HCID 20070560, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium hydride (0.5 g, 0.019 mol) was suspended in dry tetrahydrofuran followed by addition of N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide and a gas was evolved. The reactoin was stirred for 20 minutes and then chloromethylpivalate (2.9 g, 0.019 mol) was added. The reaction was stirred for two hours until pH was near neutral, and then diluted with ether and washed with water. The ether phase was washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to give 3.4 g of a yellow oil. This was extracted with hexane leaving some residue and passed through a 1" pad of florisil. This gave an evaporation of the solvent in vacuo, 1.8 g of tht title compound as a yellow oil. The structure was confirmed by MS, IR and NMR analysis.

Workup

  1. stirringThe reaction was stirred for two hours until pH
  2. washwashed with water
  3. washThe ether phase was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-4e4a0aea87544b7b9d6003006f95c67a
Source dataset
uspto-grants-1991_02
Patent number
US04992503

Reaction notes

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