Boron trifluoride etherate → HCID 15158051, compound

HRID 1650723Notes

Reaction equation

HRID 1650723 reaction equation
[CH:1]([O:8][CH2:9][CH3:10])([O:5][CH2:6][CH3:7])OCC.B(F)(F)F.CCOCC.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26](=[O:34])[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C(N(C(C)C)CC)(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH2:9]([O:8][CH:1]([O:5][CH2:6][CH3:7])[CH:27]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[C:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=1)=[O:34])[CH3:10]

Participants

8

Reactant 5

HCID 8000Boron trifluoride etherateHCID 31214Ethyl orthoformateHCID 81531DiisopropylethylamineHCID 2384361,2-di(pyridin-2-yl)ethanoneHCID 516892Sodium Bicarbonate

Product 1

HCID 15158051HCID 15158051, compoundYield 141.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 15 mL (0.089 mol) of triethyl orthoformate in 100 mL of methylene chloride was stirred under nitrogen at -78° C. and 13.2 mL (0.108 mol) of boron trifluoride etherate was added. The solution was allowed to warm to 0° C., recooled to -78° C., and a solution of 8.0 g (0.04 mol) of 1.2-bis(2-pyridinyl)ethanone in 75 mL of methylene chloride was added, followed after 30 min by 22 mL (0.132 mol) of diisopropylethylamine in 30 mL of methylene chloride. The reaction was stirred 45 min at -78° C., poured into 400 mL of water containing 10 g of NaHCO3 and stirred 20 min. The phases were separated, the methylene chloride layer was dried over MgSO4 and stripped to yield about 17 g of crude 3,3-diethoxy-1,2-bis(2-pyridinyl)-1-propanone.

Workup

  1. customrecooled to -78° C.
  2. stirringstirred 20 min
  3. customThe phases were separated
  4. dry with materialthe methylene chloride layer was dried over MgSO4

Sources & evidence

ORD record
ord-1aae487049d244c182c83ceb84504e62
Source dataset
uspto-grants-1990_05
Patent number
US04925857

Reaction notes

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