2,2,2-Trifluoroacetophenone → HCID 14915542, compound

HRID 1749153Notes

Reaction equation

HRID 1749153 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[F:14][C:15]([F:25])([F:24])[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O>C1COCC1>[F:14][C:15]([F:24])([F:25])/[C:16](/[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[CH:3]\[C:1]#[N:2]

Participants

5

Reactant 3

HCID 99052,2,2-TrifluoroacetophenoneHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 14915542HCID 14915542, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl cyanomethylphosphonate (6.1 g, 34.5 mmol) in 15 mL of THF was added sodium hydride (60% content, 1.4 g, 34.5 mmol). The mixture was stirred at room temperature. for 2 hours. 2,2,2-Trifluoro-1-phenylethanone (3 g, 17.2 mmol) was added and the mixture was stirred for 4 hours. After evaporation of THF, the residue was taken up in ethyl acetate (100 mL) and quenched with water (50 mL). The organic phase was washed with water (100 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography (petrol ether: ethyl acetate=10:1) to afford the title compound (1.5 g, yield 29%) as an oil. LC-MS: m/z 198 (M+H).

Workup

  1. stirringthe mixture was stirred for 4 hours
  2. customAfter evaporation of THF
  3. customquenched with water (50 mL)
  4. washThe organic phase was washed with water (100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by silica gel column chromatography (petrol ether: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-b55e190702f149ed84e972aff4f853cc
Source dataset
uspto-grants-2015_10
Patent number
US09156788B2

Reaction notes

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