Boron trifluoride etherate → HCID 86714015, compound

HRID 576298Notes

Reaction equation

HRID 576298 reaction equation
[Br:1][C:2]1[C:10]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=O)=[CH:9][C:8]([Br:21])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2.C([SiH](CC)CC)C.B(F)(F)F.CCOCC.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CC#N>[Br:1][C:2]1[C:10]([CH2:11][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:9][C:8]([Br:21])=[C:7]2[C:3]=1[CH2:4][CH2:5][CH2:6]2

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 86714016HCID 86714016, compound

Product 1

HCID 86714015HCID 86714015, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a solution of ketone 5-1 (3.9 g, 9.5 mmol) in CH2Cl2/CH3CN (31 mL/31 mL) were added triethylsilane (4.8 mL, 28.5 mmol) and boron trifluoride diethyl etherate (3.7 mL, 28.5 mmol) at 0° C. under nitrogen atmosphere. The mixture was warmed up to room temperature slowly and stirred at room temperature for 15 h. To the mixture was added saturated K2CO3 solution (50 mL) slowly and the mixture was extracted with EtOAc (100 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the desired product 6 (3.2 g, 8.1 mmol, 85%).

Workup

  1. extractionthe mixture was extracted with EtOAc (100 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-51957c0fbf5045f9aa59f6d169f0d1d2
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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