1,4-Dioxane hydrochloride → HCID 59443010, compound

HRID 2380901Notes

Reaction equation

HRID 2380901 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[C:7]([C:14]([O:16]CC)=[CH2:15])[C:8]([CH3:13])([CH3:12])[O:9]2)=[CH:4][CH:3]=1.Cl.O1CCOCC1>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)=[C:7]([C:14](=[O:16])[CH3:15])[C:8]([CH3:12])([CH3:13])[O:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 59443022HCID 59443022, compound

Product 1

HCID 59443010HCID 59443010, compound

Procedure

The compound obtained in (1) described above (140 mg) and 4N hydrochloric acid-dioxane solution (5 mL) were stirred at room temperature for 2 hours. The reaction solution was concentrated in vacuo, and to the resultant residue was added a saturated aqueous solution of sodium bicarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, filtered through a column of porous diatomite (Chem Elut) and the filtrate was concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=98/2 to 90/10) to give the titled compound (121 mg) as a pale yellow powder.

Workup

  1. concentrationThe reaction solution was concentrated in vacuo
  2. additionto the resultant residue was added a saturated aqueous solution of sodium bicarbonate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. filtrationfiltered through a column of porous diatomite (Chem Elut)
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resultant residue was purified by column chromatography on silica gel (Solvent: n-hexane/ethyl acetate=98/2 to 90/10)

Sources & evidence

ORD record
ord-77765a98e2a24bb9b905187eb4498bbe
Source dataset
uspto-grants-2012_09
Patent number
US08258131B2

Reaction notes

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