Water → HCID 19600806, compound

HRID 346041Notes

Reaction equation

HRID 346041 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH:11]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:18]=2)[O:13][CH2:12]1.O>CN(C=O)C.C(Cl)Cl.C(OCC)(=O)C>[CH2:23]([O:22][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[O:13][CH2:12][CH:11]([O:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[C:20]2=[O:21])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 962WaterHCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 19600716HCID 19600716, compound

Product 1

HCID 19600806HCID 19600806, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-hydroxypyridine (8.56 g, 90.0 mmol) in 300 ml anhydrous DMF was added portionwise 3.6 g of 60% NaH in oil (90 mmol. 1.0 eq.). Stirring 0.5 hour was followed by the addition of 30.0 g (90.0 mmol, 1.0 eq.) of 3-bromo-6-benzyloxy-4-chromanone in one portion. After 1 hour, the reaction was poured into 1 liter H2O and extracted 3×250 ml ethyl acetate. The organic layers were combined, washed 1×100 ml H2O, 1×100 ml 10% LiCl and 1×100 ml brine, then dried over Na2SO4. Filtration and solvent removal afforded 40 g crude product. Silica gel chromatography with 1:4 ethyl acetate:CH2Cl2 as eluant afforded 1.13 g (3.6%) of purified title product; m.p. 133°-134° C.

Workup

  1. waitAfter 1 hour
  2. extractionextracted 3×250 ml ethyl acetate
  3. washwashed 1×100 ml H2O, 1×100 ml 10% LiCl and 1×100 ml brine
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and solvent removal
  6. customafforded 40 g crude product
  7. customof purified title product

Sources & evidence

ORD record
ord-73b33053ee754be1944b3cf16c1286c5
Source dataset
uspto-grants-1991_10
Patent number
US05059609

Reaction notes

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