Lawesson's reagent → HCID 57075471, compound

HRID 1418378Notes

Reaction equation

HRID 1418378 reaction equation
[CH2:1]1[O:20][C:4]2([CH2:9][CH2:8][N:7]([C:10](=O)[C:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=3)[CH2:6][CH2:5]2)[O:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>O1CCOCC1>[CH2:1]1[O:20][C:4]2([CH2:9][CH2:8][N:7]([C:10]([C:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=3)=[S:30])[CH2:6][CH2:5]2)[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 35370604HCID 35370604, compound

Product 1

HCID 57075471HCID 57075471, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-(4-cyanobenzoyl)-4-piperidone ethylene ketal (1.00 g, 3.68 mmol) and Lawesson's reagent (1.2 g, 2.9 mmol) in dioxane (20 ml) was heated to reflux for 1 h, cooled and evaporated. The residue was pre-absorbed on silica gel and purified by flash chromatography eluting with 25% ethyl acetate/hexane, increasing the gradient to 40% ethyl acetate/hexane, to afford the product as a yellow solid (353 mg), MS (+EI) 288 (M+), 1H NMR(CDCl3) 7.67 (2H, d, J 7 Hz), 7.36 (2H, d, J 7 Hz), 4.5-4.45 (2H, m), 4.06-3.98 (4H, m), 3.58 (2H, dd, J 6, 4.2 Hz), 1.94 (2H, t, J 6 Hz), 1.69 (2H, t, J 6 Hz).

Workup

  1. temperatureto reflux for 1 h
  2. temperaturecooled
  3. customevaporated
  4. customThe residue was pre-absorbed on silica gel
  5. custompurified by flash chromatography
  6. washeluting with 25% ethyl acetate/hexane
  7. temperatureincreasing the gradient to 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-f1aaee24ae704d56a3a907b4e1f2940a
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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