Trimethylsilyldiazomethane → HCID 44248134, compound

HRID 133847Notes

Reaction equation

HRID 133847 reaction equation
[C:1]1([C:7]([CH3:14])([CH3:13])[C:8](=[O:12])[C:9]([O-:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][Si](C=[N+]=[N-])(C)C>CCOCC.CO>[C:1]1([C:7]([CH3:14])([CH3:13])[C:8](=[O:12])[C:9]([O:11][CH3:15])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 86596612HCID 86596612, compound

Product 1

HCID 44248134HCID 44248134, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a 0° C. (ice water bath) solution of 3-phenyl-3-methyl-2-oxobutanoate (9.0 g, 47 mmol, from Reference Example 35) in ether (40 mL) and methanol (60 mL). Trimethylsilyl diazomethane (2.0 M solution in hexanes, 35 mL, 70 mmol, Aldrich) is added dropwise until the evolution of gas ceased and the yellow color of the reagent persisted in solution. The solvents are evaporated under reduced pressure and the residue is taken up in ether/hexanes (1:1) and washed with 2% aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. The combined extracts are then dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a straw-colored liquid (8.5 g, 88%). MS (ES+): (M+H)=206.9

Workup

  1. customTo a 0° C.
  2. customThe solvents are evaporated under reduced pressure
  3. washwashed with 2% aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
  4. dry with materialThe combined extracts are then dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e0a2d7d1976042c6858843283d4c7d3d
Source dataset
uspto-grants-2008_06
Patent number
US07390910B2

Reaction notes

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