Tetrahydrofuran → HCID 86669800, compound

HRID 1615546Notes

Reaction equation

HRID 1615546 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]3[CH:15]=[CH:16][S:17][C:13]=3[C:12](=O)[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].O1CCCC1.C([O-])(=O)C.[Na+].Cl.[NH2:30][OH:31]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]3[CH:15]=[CH:16][S:17][C:13]=3[C:12](=[N:30][OH:31])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 68183036HCID 68183036, compound

Product 1

HCID 86669800HCID 86669800, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100 mL round bottomed flask charged with 4-(3,4-dichlorophenyl)-5,6-dihydro-1-benzothiophen-7(4H)-one (1.29 g, 4.34 mmol), tetrahydrofuran (11.0 mL) and ethanol (12.5 mL). The mixture was stirred and sodium acetate (1.117 g, 13.62 mmol) and hydroxylamine hydrochloride (0.9242 g, 13.30 mmol) were added. The mixture was stirred for 16 h at 50° C. under an atmosphere of Nitrogen. The reaction was then cooled to rt, giving a pale yellow solution with much white ppt. The reaction was quenched into ˜75 ml saline solution w/stirring and the resulting mixture was transferred to a separatory funnel and extracted with ethyl acetate (2×). the extracts were combined, washed with saline, dried over sodium sulfate, filtered, and evaporated to leave 1.27 g (94% yield) product as pale yellow powder. LCMS: (FA) ES+ 312, 314. 1H NMR indicated that the product was an ˜3:1 mixture of geometric oxime isomers.

Workup

  1. stirringThe mixture was stirred for 16 h at 50° C. under an atmosphere of Nitrogen
  2. customgiving a pale yellow solution with much white ppt
  3. customThe reaction was quenched into ˜75 ml saline solution
  4. stirringw/stirring
  5. customthe resulting mixture was transferred to a separatory funnel
  6. extractionextracted with ethyl acetate (2×)
  7. washwashed with saline
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-d64f6e51429d4338b725921f75747597
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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