Sodium hydride → HCID 10444074, compound

HRID 1494078Notes

Reaction equation

HRID 1494078 reaction equation
Br[CH:2]([CH:11]([OH:18])[C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[H-].[Na+]>C1COCC1.C(OCC)(=O)C>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH:11]2[CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])[O:18]2)[CH:13]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 14986641HCID 14986641, compound

Product 1

HCID 10444074HCID 10444074, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

16.3 g of methyl 6-bromo-7-hydroxy-7-(3-pyridyl)-heptanoate is dissolved in 200 mL of THF and 4.5 g of 50% sodium hydride added in portions. After stirring at room temperature for 3 hours, the reaction is diluted with ethyl acetate, filtered and concentrated to give crude product which is further purified by column chromatography on silica gel using ethyl acetate as eluent to yield 2-(3-pyridyl)-3-(4-methoxycarbonylbutyl)-oxirane.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customto give crude product which
  4. customis further purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-7cebb7f39df84ab78f0cc04adb80b6b7
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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