Triethylborane → HCID 22911977, compound

HRID 1378591Notes

Reaction equation

HRID 1378591 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[S:9][C:10]([C:20]2[CH:25]=[CH:24][C:23]([S:26](C)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:12]=1.C([Mg]Cl)CCC.C(B(CC)CC)C.C([O-])(=O)C.[Na+].[NH2:48]OS(O)(=O)=O>O1CCCC1.C(OCC)(=O)C.O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]2[N:12]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[S:9][C:10]=2[C:20]2[CH:25]=[CH:24][C:23]([S:26]([NH2:48])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:14][CH:15]=1

Participants

9

Reactant 5

HCID 7357TriethylboraneHCID 76284hydroxylamine-O-sulfonic acidHCID 517045Sodium AcetateHCID 9933112HCID 9933112, compoundHCID 178418265HCID 178418265, compound

Product 1

HCID 22911977HCID 22911977, compoundYield 52.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the methyl sulfone (Example 16) (0.21 g, 0.47 mmol) in tetrahydrofuran (THF) (5 mL) at 0° C. under nitrogen was added 2M n-butyl magnesium chloride in THF (1.0 mL, 2.0 mmol) slowly, via syringe, and the mixture stirred at 0° C. for 30 minutes and then at room temperature (25° C.) for 2 hours. After cooling to 0° C., a 1.0M solution of triethyl borane in THF (2.5 mL, 2.5 mmol) was added and the mixture warmed to room temperature and stirred for 2 hours, and then heated to reflux overnight (18 hours). After cooling to room temperature and stirring for 3 hours, water (3 mL) was added followed by sodium acetate (1.2 g) and hydroxylamine-O-sulfonic acid (0.82 g). After stirring at room temperature overnight, the mixture was poured into 3 volumes of ethyl acetate, and the organic layer washed with water and brine and dried over MgSO4. After solvent removal, the white solids (a mixture of product and starting material) was recrystalized from ethyl acetate/hexane to provide 0.11 g of a white solid. Anal. Calc'd for C21H14N2O2S2FCl: C, 56.69; H, 3.17; N, 6.30. Found: C, 55.99; H, 2.97; N, 6.15.

Workup

  1. waitat room temperature (25° C.) for 2 hours
  2. temperatureAfter cooling to 0° C.
  3. temperaturethe mixture warmed to room temperature
  4. stirringstirred for 2 hours
  5. temperatureheated
  6. temperatureto reflux overnight (18 hours)
  7. temperatureAfter cooling to room temperature
  8. stirringstirring for 3 hours
  9. stirringAfter stirring at room temperature overnight
  10. washthe organic layer washed with water and brine
  11. dry with materialdried over MgSO4
  12. customAfter solvent removal
  13. additionthe white solids (a mixture of product and starting material)
  14. customwas recrystalized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0c946606c86644a28ed19a4ee17bda14
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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