Sodium hydride → HCID 14517463, compound

HRID 1033228Notes

Reaction equation

HRID 1033228 reaction equation
[H-].[Na+].Br[CH:4]1[CH:13]([OH:14])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:11]=2)[O:6][C:5]1([CH3:25])[CH3:24]>CS(C)=O>[O:14]1[CH:13]2[CH:4]1[C:5]([CH3:25])([CH3:24])[O:6][C:7]1[C:12]2=[CH:11][C:10]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 14517462HCID 14517462, compound

Product 1

HCID 14517463HCID 14517463, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To 100 ml of absolute DMSO are added 1.8 g (0.06 mol) of NaH as an 80% strength suspension in oil and, dropwise, 20 g of 3-bromo-4-hydroxy-2,2-dimethyl-6-phenylsulfonylchroman, dissolved in 80 ml of DMSO, the reaction temperature being kept at 25°-28° C. After stirring at room temperature for 2 hours, the mixture is stirred into ice water and the resulting precipitate is filtered off with suction. Further purification can be achieved by dissolving the crude product in ethyl acetate and treating it with active carbon. After evaporating the solvent, the residue is treated with diisopropyl ether until crystallization starts. Yield: 14.5 g; m.p.: 103°-105° C.

Workup

  1. custombeing kept at 25°-28° C
  2. filtrationthe resulting precipitate is filtered off with suction
  3. customFurther purification
  4. dissolutionby dissolving the crude product in ethyl acetate
  5. additiontreating it with active carbon
  6. customAfter evaporating the solvent
  7. additionthe residue is treated with diisopropyl ether until crystallization

Sources & evidence

ORD record
ord-90bda2fb57834c8ebd130676b7b4444b
Source dataset
uspto-grants-1994_05
Patent number
US05310753

Reaction notes

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