HCID 11807573, compound → HCID 10945871, compound

HRID 2227429Notes

Reaction equation

HRID 2227429 reaction equation
[O-:1]Cl.[Na+].[CH3:4][O:5][CH:6]([O:21][CH3:22])[C@@:7]1([CH3:20])[CH:12]=[CH:11][C:10]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:9]=2[O:8]1>C(Cl)Cl>[CH3:22][O:21][CH:6]([O:5][CH3:4])[C@@:7]1([CH3:20])[C@H:12]2[O:1][C@H:11]2[C:10]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:9]=2[O:8]1

Participants

4

Reactant 2

HCID 11807573HCID 11807573, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 10945871HCID 10945871, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the pre-cooled solution of 0.55 M NaOCl (55 mL, 30.0 mmol) and of 0.05 M Na2HPO4 (21.5 mL) at 0° C., (2R)-2-dimethoxymethyl-2-methyl-6-nitro-2H-1-benzopyran n(2 g, 7.5 mmol) and (R, R) Jacobson's catalyst (477.5 mg, 0.75 mmol) in CH2Cl2 (10 mL) was added. The reaction mixture was stirred at rt for 8 hr and then filtered through Celite to remove the jacobson's catalyst. The layer was separated and the organic layer was washed with brine, dried (Na2SO4), filtered, then concentrated under reduced pressure. The residue was purified by silicagel column chromatography (n-hexane:ethyl acetate=4:1) to give the desired compound (1.64 g, 77%) as a light yellow solid.

Workup

  1. filtrationfiltered through Celite
  2. customto remove the jacobson's catalyst
  3. customThe layer was separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silicagel column chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-b115c09af05e48119dcee204ef2d367f
Source dataset
uspto-grants-2002_07
Patent number
US06413983B1

Reaction notes

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