Hydrochloric Acid → [5-(2-Ethoxyethoxy)-2-pyridyl]acetone

HRID 1086249Notes

Reaction equation

HRID 1086249 reaction equation
C([Li])CCC.[CH2:6]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[N:16][CH:17]=1)[CH3:7].CN(C)[C:21](=[O:23])[CH3:22].Cl>CCCCCC.O1CCCC1>[CH2:6]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:21](=[O:23])[CH3:22])=[N:16][CH:17]=1)[CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31374DimethylacetamideHCID 150671045-(2-Ethoxyethoxy)-2-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 15067111[5-(2-Ethoxyethoxy)-2-pyridyl]acetone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolvent

Procedure

2.5 ml of a 2.5 M solution of n-butyllithium in hexane are added dropwise at 5° C. to a solution of 1 g (5.5 mmol) of 5-(2-ethoxyethoxy)-2-methylpyridine in 20 ml of tetrahydrofuran. The mixture is stirred at 0°-5° C. for 10 minutes and then 530 mg (6 mmol) of N,N-dimethylacetamide dissolved in a little tetrahydrofuran are added. After stirring at room temperature for 90 minutes, the pH is adjusted to 5 with dilute hydrochloric acid and the tetrahydrofuran is stripped off. The residue is extracted with ethyl acetate, and the organic phase is dried with sodium sulphate and evaporated. Yield: 580 mg (47% of theory), content according to GC/MS: 75%.

Workup

  1. additionare added
  2. stirringAfter stirring at room temperature for 90 minutes
  3. extractionThe residue is extracted with ethyl acetate
  4. dry with materialthe organic phase is dried with sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-c33e8bb245504f4dae515bdc12f81a24
Source dataset
uspto-grants-1991_07
Patent number
US05028617

Reaction notes

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