Boron trifluoride etherate → HCID 86714015, compound

HRID 2206671Notes

Reaction equation

HRID 2206671 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-6dc880ff88314ad1add6b34a015c16a6
Source dataset
uspto-grants-2016_06
Patent number
US09371303B2

Reaction notes

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