Sodium hydride → HCID 60077989, compound

HRID 2085170Notes

Reaction equation

HRID 2085170 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-e1c6753fe53f4a9c8557c8780c49e080
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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