Triethylamine → HCID 53942881, compound

HRID 1604541Notes

Reaction equation

HRID 1604541 reaction equation
C[Si]([CH:5]=[N+:6]=[N-:7])(C)C.C([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])C.Cl.[Cl-].[O:17]1C[CH2:20][CH2:19][CH:18]1CC#N>CCCCCC>[N+:6](=[CH:5][C:18]([C:19]1[C:13]([CH3:14])=[N:10][CH:11]=[CH:12][CH:20]=1)=[O:17])=[N-:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 167693TrimethylsilyldiazomethaneHCID 86754879HCID 86754879, compound

Product 1

HCID 53942881HCID 53942881, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 10% trimethylsilyldiazomethane in hexane (4.2 ml) and triethylamine (527 mg) in tetrahydrofuranacetonitrile chloride hydrochloride (500 mg) in an ice water bath. The mixture was stirred for 7 hours in an ice water bath and allowed to stand for 18 hours at 0° C., then evaporated in vacuo. Saturated aqueous sodium bicarbonate solution was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over magnesium sulfate. Evaporation of the solvent gave crude 3-diazoacetyl-2-methylpyridine as an yellow oil.

Workup

  1. waitto stand for 18 hours at 0° C.
  2. customevaporated in vacuo
  3. additionSaturated aqueous sodium bicarbonate solution was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f3414646ec634bea8eb3228cbc125cbf
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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