Sodium Hydroxide → HCID 9817280, compound

HRID 2218336Notes

Reaction equation

HRID 2218336 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].C([O:13][C:14]1[C:24]2[CH2:23][CH2:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[O:19][C:18]=2[CH:17]=[C:16]([O:29]C(=O)C)[CH:15]=1)(=O)C.[OH-].[Na+]>C(Cl)Cl.CO>[C:5]([C:26]1[CH:27]=[CH:28][C:20]2[O:19][C:18]3[CH:17]=[C:16]([OH:29])[CH:15]=[C:14]([OH:13])[C:24]=3[CH2:23][CH2:22][C:21]=2[CH:25]=1)(=[O:8])[CH2:6][CH3:7]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 5976975410,11-Dihydrodibenz[b,f]oxepin-1,3-diol diacetate

Product 1

HCID 9817280HCID 9817280, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of aluminum chloride (1 g, 7.5 mmol) in anhydrous methylene chloride (3 mL) was added propionyl chloride (668 μL, 7.7 mmol) and stirred at room temperature for one hour. This solution was added dropwise to a solution of 10,11-dihydrodibenz[b,f]oxepin-1,3-diol diacetate (62) (300 mg, 0.96 mmol) in methylene chloride (5 mL) at 0° C. and stirred at room temperature for one hour. To the reaction solution was added dropwise methanol (10 mL) at 0° C. and a 20% sodium hydroxide aqueous solution (3 mL) was added thereto and stirred at room temperature for 30 minutes. After completion of the reaction, the reaction solution was poured into hydrochloric acid-ice water and extracted with ethyl acetate, and the organic layer was washed with water and then with a saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica-gel column chromatography (developing solvent; hexane:ethyl acetate=2:1), and recrystallization was carried out from ethyl acetate and hexane to obtain 190 mg (yield 70%) of skin-colored needles of the title compound.

Workup

  1. stirringstirred at room temperature for one hour
  2. stirringstirred at room temperature for 30 minutes
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was washed with water
  6. dry with materialwith a saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica-gel column chromatography (developing solvent; hexane:ethyl acetate=2:1), and recrystallization

Sources & evidence

ORD record
ord-78301a62489c47efb9626185a3e5fe5e
Source dataset
uspto-grants-2008_08
Patent number
US07410997B2

Reaction notes

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