Hydrochloric Acid → HCID 18325133, compound

HRID 1250945Notes

Reaction equation

HRID 1250945 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:18]=[CH:17][C:16]2[C:6](=[C:7]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[C:8]3[C:12](=O)[O:11][C:10](=[O:14])[C:9]=3[CH:15]=2)[CH:5]=1.Cl>C(COC)OC.C1COCC1>[Cl:3][C:4]1[CH:18]=[CH:17][C:16]2[C:6](=[C:7]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[C:8]3[CH2:12][O:11][C:10](=[O:14])[C:9]=3[CH:15]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3484336-Chloro-4-(4-chlorophenyl)naphtho[2,3-c]furan-1,3-dioneHCID 4311764Sodium borohydride

Product 1

HCID 18325133HCID 18325133, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of sodium borohydride (0.5 g) in dimethoxyethane (20 ml), a solution of 6-chloro-4-(4-chlorophenyl) naphtho[2,3-c]furan-1,3-dione (1.0 g) in THF (20 ml) was added dropwise, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into 1N hydrochloric acid to stop the reaction; the product was extracted with ethyl acetate. After being washed with water, the extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (eluent: hexane−ethyl acetate=3:1) and recrystallized from THF to yield the title compound (300 mg).

Workup

  1. customthe reaction
  2. extractionthe product was extracted with ethyl acetate
  3. washAfter being washed with water
  4. dry with materialthe extract was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by silica gel column chromatography (eluent: hexane−ethyl acetate=3:1)
  8. customrecrystallized from THF

Sources & evidence

ORD record
ord-3a390c72ebb94fd8accdaa722bda5107
Source dataset
uspto-grants-2002_01
Patent number
US06340704B1

Reaction notes

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