Acetone → HCID 86747883, compound

HRID 1034209Notes

Reaction equation

HRID 1034209 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:7]1[CH2:8][NH:9][CH2:10][CH2:11][CH:12]=1)[C:5]#[N:6].[C:13](=[O:16])([O-:15])[O-].[K+].[K+].I[CH2:20][CH3:21].CC(C)=[O:24]>>[C:1]([OH:2])(=[O:24])[C:13]([OH:15])=[O:16].[CH3:1][O:2][N:3]=[C:4]([C:7]1[CH2:8][N:9]([CH2:20][CH3:21])[CH2:10][CH2:11][CH:12]=1)[C:5]#[N:6]

Participants

5

Reactant 4

HCID 180AcetoneHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 54399635HCID 54399635, compound

Product 1

HCID 86747883HCID 86747883, compoundYield 94%

Procedure

To a vigorously stirred mixture of α-(methoxyimino)-α-(1,2,5,6-tetrahydropyridin-3-yl)acetonitrile (E10) (1.1 g, 0.0067 mol) and potassium carbonate (2.0 g, 0.0145 mol) in acetone (50 ml) at room temperature was added iodoethane (1.17 g, 0.0075 mol). After 4 hrs the mixture was concentrated in vacuo and the residue partitioned between water (25 ml) and chloroform (3×50 ml) The combined organic extracts were dried (Na2SO4) and evaporated to a residue which was purified by column chromatography on silica gel eluting with 0-2% methanol/chloroform to give the free base of the title compound (E11) (1.22 g, 94%). A portion of this was treated with anhydrous oxalic acid to give a solid which crystalised from ethanol/diethyl ether to afford the title compound (E11) as a white solid m.p. 155°-6° C.

Workup

  1. concentrationAfter 4 hrs the mixture was concentrated in vacuo
  2. customthe residue partitioned between water (25 ml) and chloroform (3×50 ml) The combined organic extracts
  3. dry with materialwere dried (Na2SO4)
  4. customevaporated to a residue which
  5. customwas purified by column chromatography on silica gel eluting with 0-2% methanol/chloroform

Sources & evidence

ORD record
ord-66ce3663aed746d797f11d1d73618690
Source dataset
uspto-grants-1994_05
Patent number
US05314901

Reaction notes

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