Sodium hydride → HCID 60077989, compound

HRID 460598Notes

Reaction equation

HRID 460598 reaction equation
[H-].[Na+].[CH3:3][C:4]([C:6]1[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:14]([OH:15])[C:8]=2[C:7]=1[CH3:16])=[O:5].S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:21][C@H:22]1[O:24][CH2:23]1)(=O)=O>CN(C=O)C>[CH3:3][C:4]([C:6]1[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH2:21][C@H:22]3[O:24][CH2:23]3)[C:8]=2[C:7]=1[CH3:16])=[O:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoateHCID 13849498HCID 13849498, compound

Product 1

HCID 60077989HCID 60077989, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a suspension (60 ml) of sodium hydride (1.4 g) in DMF was added dropwise a solution (30 ml) of 4-hydroxy-3-methylbenzo(b)furan-2-yl methyl ketone (6.1 g) in DMF under ice-cooling and the mixture was stirred at room temperature for 30 min. To this reaction mixture was added dropwise under ice-cooling a solution (30 ml) of (S)-glycidyl nosylate (9.1 g) in DMF, and the mixture was stirred for 2 hr. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (3.1 g) as pale-yellow crystals.

Workup

  1. temperaturecooling
  2. additionTo this reaction mixture was added dropwise under ice-
  3. stirringthe mixture was stirred for 2 hr
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b50a5949c3f346e38f00f5ce8b0013bb
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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