3',4',5'-Trimethoxyacetophenone → HCID 69156528, compound

HRID 497033Notes

Reaction equation

HRID 497033 reaction equation
[H-].[Na+].P([O-])([O-])(O[CH:6]([CH2:9][CH3:10])[C:7]#[N:8])=O.CC([C:16]1[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=1)=O>C1COCC1>[CH3:27][O:26][C:18]1[CH:17]=[C:16]([C:9]([CH3:10])=[CH:6][C:7]#[N:8])[CH:21]=[C:20]([O:22][CH3:23])[C:19]=1[O:24][CH3:25]

Participants

5

Reactant 3

HCID 143453',4',5'-TrimethoxyacetophenoneHCID 24758Sodium hydrideHCID 131725160HCID 131725160, compound

Product 1

HCID 69156528HCID 69156528, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 60% NaH (1.46 g, 61.1 mmol) in THF at 0° C. was added 10.0 g (56.4 mmol) of ethyl(cyanomethyl) phosphate. A solution of 9.88 g (47.0 mmol) of 3,4,5-trimethoxyacetophenone in THF was added precipitating a yellow solid. The mixture was stirred at room temperature for 30 minutes, quenched with water, and extracted with ethyl acetate. The organic extract was washed with brine, dried (MgSO4), and evaporated in vacuo to afford 9.32 g (85%) of 16 as a yellow oil.

Workup

  1. customprecipitating a yellow solid
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-afaa4a482e9e4cb58921d7e078554d27
Source dataset
uspto-grants-2005_09
Patent number
US06949544B2

Reaction notes

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