Acetyl chloride → HCID 54026535, compound

HRID 1708116Notes

Reaction equation

HRID 1708116 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:7]1[CH2:8][N:9]([OH:13])[CH2:10][CH2:11][CH:12]=1)[C:5]#[N:6].C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22]>O1CCCC1>[CH3:1][O:2][N:3]=[C:4]([C:7]1[CH2:8][N:9]([O:13][C:21](=[O:23])[CH3:22])[CH2:10][CH2:11][CH:12]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 54140687HCID 54140687, compound

Product 1

HCID 54026535HCID 54026535, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

α-(Methoxyimino)-α-(1-hydroxy-1,2,5,6-tetrahydropyridin-3-yl)acetonitrile (E2) (0.5 g, 0.0028 moles) was dissolved in dry tetrahydrofuran (20 ml) and treated with triethylamine (0.43 ml, 0.0031 moles) with stirring at room temperature. This mixture was then treated with acetyl chloride (0.22 ml, 0.0031 moles) and stirred at ambient temperature for 2 h. The mixture was filtered and the filtrate evaporated to dryness. The residue was chromatographed on silica gel eluting with chloroform. The crystalline residue was recrystallised from 60-80 petrol to give the title compound (E10) as an off-white crystalline solid (0.234 g, 38%) m.p. 87°-8° C.

Workup

  1. stirringstirred at ambient temperature for 2 h
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated to dryness
  4. customThe residue was chromatographed on silica gel eluting with chloroform
  5. customThe crystalline residue was recrystallised from 60-80 petrol

Sources & evidence

ORD record
ord-e38717ea509044838eb9d335d273b62a
Source dataset
uspto-grants-1994_10
Patent number
US05356914

Reaction notes

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