Sodium hydride → 3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-pyrano[3,2-c]pyridine

HRID 2106723Notes

Reaction equation

HRID 2106723 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:16])[C@@H:13](Br)[C@H:12]([OH:15])[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[O:5]1>CS(C)=O>[CH3:3][C:4]1([CH3:16])[CH:13]2[O:15][CH:12]2[C:11]2[C:6](=[CH:7][CH:8]=[N:9][CH:10]=2)[O:5]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67937472HCID 67937472, compound

Product 1

HCID 108560303,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-pyrano[3,2-c]pyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.4 g of a 60% strength oil dispersion of NaH are added to a solution of 2.82 g of trans-2,2-dimethyl-3-bromo-6-azachroman-4-ol in 15 ml of DMSO, with stirring. The mixture is stirred for 1 hour, 2,2-dimethyl-3,4-epoxy-6-azachroman being intermediately formed. 1.43 g of 1H-2-pyridone and a further 0.5 g of NaH dispersion are added and the mixture is stirred at 20° for 16 hours. Working up analogously to Example 1 gives "A", melting point 208°-210°.

Workup

  1. stirringThe mixture is stirred for 1 hour

Sources & evidence

ORD record
ord-1d40bf4095ec40738b086f1dc406b398
Source dataset
uspto-grants-1990_06
Patent number
US04931454

Reaction notes

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