Boron trifluoride etherate → HCID 23437833, compound

HRID 632472Notes

Reaction equation

HRID 632472 reaction equation
B(F)(F)F.CCOCC.[I:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=O)=[CH:13][CH:12]=1.[BH4-].[Na+]>C1COCC1>[I:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 23438120HCID 23438120, compound

Product 1

HCID 23437833HCID 23437833, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

BF3.Et2O (6.43 g, 45.3 mmol) was added to a solution of 2-(4-iodo-phenyl)-1-morpholin-4-yl-ethanone (3.0 g, 9.06 mmol) in THF (75 mL) at 0° C., stirred for 30 min, then NaBH4 (1.72 g, 45.3 mmol) was added at 0° C. The reaction mixture was slowly warmed to RT. After 16 h the reaction mixture was cooled to 0° C., quenched with ice-cold water, extracted with EtOAc (2×100 mL). The organic layer was washed with brine solution (50 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure. The crude compound was purified by column chromatography using 100-200 mesh silica gel, eluted with 20-30% EtOAc in pet-ether to afford 1.56 g (Yield: 54.3%) of the title compound as a yellow solid.

Workup

  1. temperatureAfter 16 h the reaction mixture was cooled to 0° C.
  2. customquenched with ice-cold water
  3. extractionextracted with EtOAc (2×100 mL)
  4. washThe organic layer was washed with brine solution (50 mL)
  5. dry with materialdried over anhydrous Na2SO4 and solvent
  6. customwas evaporated under reduced pressure
  7. customThe crude compound was purified by column chromatography
  8. washeluted with 20-30% EtOAc in pet-ether

Sources & evidence

ORD record
ord-bc2f31fd6d744809b76b699e09f9d45a
Source dataset
uspto-grants-2016_04
Patent number
US09321748B2

Reaction notes

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