Ethyl isobutyrate → HCID 19854762, compound

HRID 1649838Notes

Reaction equation

HRID 1649838 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[C:13]([O:18][CH2:19][CH3:20])(=[O:17])[CH:14]([CH3:16])[CH3:15].Cl.Cl[CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.[Cl-].[NH4+]>CCCCCC.C1COCC1.CN1C(=O)N(C)CCC1>[N:26]1[CH:27]=[CH:28][CH:29]=[C:24]([CH2:23][C:14]([CH3:16])([CH3:15])[C:13]([O:18][CH2:19][CH3:20])=[O:17])[CH:25]=1

Participants

9

Reactant 5

HCID 7342Ethyl isobutyrateHCID 7912DiisopropylamineHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 19854762HCID 19854762, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
-70 °C

Procedure

1.5M Butyllithium in hexane (20 ml) was added dropwise, under argon, to a stirred, cooled (-20° C.) solution of diisopropylamine (4.2 ml) in THF (50 ml). After 10 minutes the mixture was cooled to -70° C. and ethyl isobutyrate (3.99 ml) was added dropwise keeping the temperature <-60° C. Stirring was continued for 20 minutes after completion of the addition then DMPU (15 ml) was added followed by solid 3-chloromethylpyridine hydrochloride (2.0 g). After stirring for 30 minutes at -70° C., the mixture was allowed to warm to 4° C. and was then added to saturated ammonium chloride solution (200 ml). The mixture obtained was extracted with ether (3×100 ml). The combined extracts were washed with brine (50 ml), dried (MgSO4) and evaporated. The residue was purified by flash chromatrography using ether as eluant to give ethyl 3-(3-pyridyl)-2,2-dimethylpropionate (A) as a clear oil (2.12 g); NMR (CDCl3): 1.20 (6H, s), 1.23 (3H, t J=7 Hz), 2.87 (2H, s), 4.12 (2H, q J=7 Hz). 7.20 (1H, J=7, 5 Hz), 7.46 (1H, dt J=7, 1 Hz), 8.40 (1H, d J=1.5 Hz), 8.47 (1H, dd J=5, 1.5 Hz).

Workup

  1. customthe temperature <-60° C
  2. additionafter completion of the addition
  3. stirringAfter stirring for 30 minutes at -70° C.
  4. temperatureto warm to 4° C.
  5. customThe mixture obtained
  6. extractionwas extracted with ether (3×100 ml)
  7. washThe combined extracts were washed with brine (50 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was purified by flash chromatrography

Sources & evidence

ORD record
ord-fac38b99679447b5a01b52e660eaf509
Source dataset
uspto-grants-1990_05
Patent number
US04921866

Reaction notes

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