Dimethylformamide diethylacetal → HCID 68807259, compound

HRID 526430Notes

Reaction equation

HRID 526430 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:3][CH:2]=1.C(O[CH:16](OCC)[N:17]([CH3:19])[CH3:18])C>CN(C=O)C>[CH3:16][N:17]([CH3:19])[CH:18]=[C:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 736321Ethyl pyridine-4-acetate

Product 1

HCID 68807259HCID 68807259, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combined ethyl 2-(pyridin-4-yl)acetate (0.927 mL, 6.05 mmol) and 1,1-diethoxy-N,N-dimethylmethanamine (5.19 mL, 30.3 mmol) in DMF (3.03 mL) and heated to 100° C. for 6 hours. The reaction mixture was concentrated, diluted with 50 mL dichloromethane, and washed twice with 50 mL water. The organic layer was collected, dried over magnesium sulfate, filtered and concentrated to give a residue which was purified on a 60 g NH silica gel column eluted with hexanes and EtOAc to give the title compound (1.333 g, 76%) as a yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 1.13 (t, J=7.1 Hz, 3H) 2.67 (s, 6H) 4.06 (q, J=7.1 Hz, 2H) 6.98-7.12 (m, 2H) 7.56 (s, 1H) 8.29-8.53 (m, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with 50 mL dichloromethane
  3. washwashed twice with 50 mL water
  4. customThe organic layer was collected
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a residue which
  9. customwas purified on a 60 g NH silica gel column
  10. washeluted with hexanes and EtOAc

Sources & evidence

ORD record
ord-906ff340aaac4124a83b95f01a62dfc5
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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