HCID 11076344, compound → HCID 11097971, compound

HRID 2227428Notes

Reaction equation

HRID 2227428 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 11076344HCID 11076344, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 11097971HCID 11097971, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the pre-cooled solution of 0.55 M NaOCl (110 mL, 60.0 mmol) and 0.05 M Na2HPO4 (43 mL) at 0° C., was added (2S)-2-dimethoxymethyl-2-methyl-6-nitro-2H-1-benzopyran (4 g, 15 mmol) and (R,R) Jacobson's catalyst (477.5 mg, 0.75 mmol) in CH2Cl2 (20 mL). 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 (3.24 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-d32c090f5f6e4f4ba4c9a89a5f17a8ae
Source dataset
uspto-grants-2002_07
Patent number
US06413983B1

Reaction notes

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