Boron trifluoride etherate → HCID 66692858, compound

HRID 1469179Notes

Reaction equation

HRID 1469179 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH3:7])=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=O)[CH:3]=1.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[S:6][C:5]([CH3:7])=[C:4]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 65639687HCID 65639687, compound

Product 1

HCID 66692858HCID 66692858, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a solution of methanone 9 (11.7 g, 37.6 mmol) in CH2Cl2/CH3CN (90 mL/90 mL) were added triethylsilane (15.0 mL, 94.0 mmol) and boron trifluoride diethyl etherate (12.0 mL, 94.0 mmol) at 0° C. The mixture was warmed up to room temperature slowly and stirred at room temperature for 15 hours. To the mixture was added aq. saturated K2CO3 solution (100 mL) slowly and extracted with EtOAc (100 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the desired product 10 (11.2 g, 100%).

Workup

  1. extractionextracted with EtOAc (100 mL×2)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica column chromatography (Biotage)

Sources & evidence

ORD record
ord-51065575034f429dbc1ec4c6d51d74d4
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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