Sodium hydride → 2,2-Dimethyl-3,4-epoxy-6-cyanochroman

HRID 1637210Notes

Reaction equation

HRID 1637210 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH3:18])[C@@H:13](Br)[C@H:12]([OH:15])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:16]#[N:17])[CH:10]=2)[O:5]1>CS(C)=O>[CH3:3][C:4]1([CH3:18])[CH:13]2[O:15][CH:12]2[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:16]#[N:17])[CH:10]=2)[O:5]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 6932483trans-2,2-Dimethyl-3-bromo-6-cyanochroman-4-ol

Product 1

HCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

0.4 g of a 60% dispersion of NaH in oil is added with stirring to a solution of 2.82 g of trans-2,2-dimethyl-3-bromo-6-cyanochroman-4-ol in 15 ml of DMSO. The mixture is stirred for 1 hour, 2,2-dimethyl-3,4-epoxy-6-cyanochroman being formed as an intermediate. 1.43 9 of 1H-2-pyridone and a further 0.5 g of the NaH dispersion are added and the mixture is stirred for 16 hours at 20°. Working up analogously to Example 1 gives "A" (m.p. 146-148°) and "B" (m.p. 244°).

Sources & evidence

ORD record
ord-201414944ce544cb81d114450a1a11f7
Source dataset
uspto-grants-2000_03
Patent number
US06040308

Reaction notes

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