Water → HCID 19600806, compound

HRID 487900Notes

Reaction equation

HRID 487900 reaction equation
[OH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Na+].[CH2:10]([O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[O:24][CH2:23][CH:22](Br)[C:21]2=[O:29])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>CN(C)C=O>[CH2:10]([O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[O:24][CH2:23][CH:22]([O:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[C:21]2=[O:29])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

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

Product 1

HCID 19600806HCID 19600806, compoundYield 0.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-hydroxypyridine (8.56 g, 0.090 mol) in 300 ml of dimethylformamide was added NaH (60% in oil, 3.6 g, 0.090 mol). After stirring 0.5 hour, 6-benzyloxy-3-bromo-4-chromanone (30.0 g., 0.090 mol) was added in one portion. After stirring for 1 hour, the reaction mixture was poured into 1 liter of water and extracted 3×250 ml of ethyl acetate. The organic layers were combined, washed 1×100 ml H2O, 1×100 ml 10% LiCl and 1×100 ml brine, dried (Na2SO4) and stripped to yield 40 g of crude title product, which was chromatographed on silica gel using 1:4 ethyl acetate:CH2Cl2 as eluant to yield 1.13 g of purified title product as an off-white powder; mp 133°-134° C. A portion (290 mg) was recrystallized from isopropyl ether to yield 240 mg of white powder.

Workup

  1. stirringAfter stirring for 1 hour
  2. extractionextracted 3×250 ml of ethyl acetate
  3. washwashed 1×100 ml H2O, 1×100 ml 10% LiCl and 1×100 ml brine
  4. dry with materialdried (Na2SO4)
  5. customto yield 40 g of crude title product, which
  6. customwas chromatographed on silica gel using 1:4 ethyl acetate
  7. customCH2Cl2 as eluant to yield 1.13 g
  8. customof purified title product as an off-white powder
  9. customA portion (290 mg) was recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-eb6358dc6f84414ba45820fa30c2a073
Source dataset
uspto-grants-1994_03
Patent number
US05298512

Reaction notes

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