Water → HCID 9909128, compound

HRID 1656453Notes

Reaction equation

HRID 1656453 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[O:10]1[CH:16]2[CH:11]1[C:12]([CH3:29])([CH3:28])[O:13][C:14]1[CH:20]=[CH:19][C:18]([S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])=[CH:17][C:15]=12.O>CS(C)=O>[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[C@@H:16]1[C:15]2[CH:17]=[C:18]([S:21]([C:24]([F:25])([F:27])[F:26])(=[O:23])=[O:22])[CH:19]=[CH:20][C:14]=2[O:13][C:12]([CH3:28])([CH3:29])[C@H:11]1[OH:10]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 15036013HCID 15036013, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 9909128HCID 9909128, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

105 mg of 2-hydroxypyridine were added to a suspension of 48 mg of sodium hydride (as a 55% w/w dispersion in mineral oil) in anhydrous dimethyl sulfoxide, and the resulting mixture was stirred at room temperature for 15 minutes. At the end of this time, 309 mg of 3,4-epoxy-3,4-dihydro-2,2-dimethyl-6-trifluoromethylsulfonyl-2H-1-benzopyran (prepared as described in Preparation 8) were added under an atmosphere of nitrogen and at room temperature to the mixture. The mixture was then stirred at room temperature for 24 hours, after which it was poured into water and extracted with ethyl acetate. The extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order; it was then dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 3:1 by volume mixture of ethyl acetate and cyclohexane as the eluent, to afford 95 mg of the title compound.

Workup

  1. stirringThe mixture was then stirred at room temperature for 24 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and with a saturated aqueous solution of sodium chloride, in that order
  4. dry with materialit was then dried over anhydrous sodium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customthe resulting residue was purified by column chromatography through silica gel
  7. additionby volume mixture of ethyl acetate and cyclohexane as the eluent

Sources & evidence

ORD record
ord-b9baf044bf5848cd9ea7c210c8cb055b
Source dataset
uspto-grants-1993_10
Patent number
US05254578

Reaction notes

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