Tetrahydrofuran → HCID 67168111, compound

HRID 243748Notes

Reaction equation

HRID 243748 reaction equation
C1COCC1.Br.[CH3:7][N:8]([CH2:10][CH2:11][CH2:12][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:9].O=[C:33]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[CH2:40][CH2:39][C:38]2[CH:37]=[C:36]([CH:47]=[CH:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[S:35][C:34]1=2.[ClH:54].O1CCOCC1>O1CCOCC1>[ClH:54].[CH3:7][N:8]([CH3:9])[CH2:10][CH2:11]/[CH:12]=[C:33]1\[C:34]2[S:35][C:36](/[CH:47]=[CH:48]/[C:49]([O:51][CH2:52][CH3:53])=[O:50])=[CH:37][C:38]=2[CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]\1=2

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 204431481,4-Dioxane hydrochlorideHCID 67168262HCID 67168262, compoundHCID 86653808HCID 86653808, compound

Product 1

HCID 67168111HCID 67168111, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 1.6 mol/L n-butyllithium-hexane solution (42 mL) was added to a THF (100 mL) solution of dimethylaminopropyltriphenylphosphonium hydrobromide (23.5 g) under ice-cooling, and the mixed solution was stirred at room temperature for 1 hour. A THF (100 mL) solution of the compound obtained in Example 1 (6.11 g) was added to this solution, and the mixture was further stirred overnight. The solvent was distilled off under a reduced pressure, an aqueous saturated ammonium chloride solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and then dried over anhydrous sodium sulfate, and the solvent was distilled off under a reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol=9:1), the purified product obtained was dissolved in 1,4-dioxane (20 mL), a 4 mol/L hydrogen chloride-dioxane solution (1.1 mL) was thereto, and the mixture was stirred at room temperature for 1 hour. The solvents were distilled off under a reduced pressure, and the precipitated crystals were filtered off and dried, to give 0.51 g (6%) of the captioned compound as a mixture of E-form and Z-form.

Workup

  1. temperaturecooling
  2. stirringthe mixture was further stirred overnight
  3. distillationThe solvent was distilled off under a reduced pressure
  4. additionan aqueous saturated ammonium chloride solution was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under a reduced pressure
  9. customThe residue was purified by silica gel column chromatography (chloroform-methanol=9:1)
  10. customthe purified product obtained
  11. stirringthe mixture was stirred at room temperature for 1 hour
  12. distillationThe solvents were distilled off under a reduced pressure
  13. filtrationthe precipitated crystals were filtered off
  14. customdried

Sources & evidence

ORD record
ord-7de585bd5bfd47bda3032c2ac7cbf4b7
Source dataset
uspto-grants-2014_02
Patent number
US08653285B2

Reaction notes

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