Dimethylformamide diethylacetal → Ethyl 3-(dimethylamino)-2-(2-methoxypyridin-4-yl)acrylate

HRID 526396Notes

Reaction equation

HRID 526396 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][N:4]=1.C(O[CH:18](OCC)[N:19]([CH3:21])[CH3:20])C>>[CH3:18][N:19]([CH3:21])[CH:20]=[C:9]([C:7]1[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 81850339Ethyl 2-(2-methoxypyridin-4-yl)acetate

Product 1

HCID 131732874Ethyl 3-(dimethylamino)-2-(2-methoxypyridin-4-yl)acrylate

Procedure

Combined ethyl 2-(2-methoxypyridin-4-yl)acetate (320 mg, 1.639 mmol) and 1,1-diethoxy-N,N-dimethylmethanamine (2079 μl, 12.13 mmol) and heated to 100° C. for 1 h then cooled to ambient temperature with stirring overnight. The reaction was concentrated in vacuo to afford a brown oil. The oil was partitioned between EtOAc and water (200 mL). The aqueous phase was back-extracted with EtOAc (2×20 mL) and the organic layers were combined, washed with brine (100 mL), dried over sodium sulfate, and concentrated to an oil in vacuo. The oil was purified by flash chromatography (100 g basic silica using a 5% to 50% EtOAc in heptanes gradient) to give the title compound as a light yellow oil. MS m/z [M+H]+ 251.1.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customto afford a brown oil
  3. customThe oil was partitioned between EtOAc and water (200 mL)
  4. extractionThe aqueous phase was back-extracted with EtOAc (2×20 mL)
  5. washwashed with brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to an oil in vacuo
  8. customThe oil was purified by flash chromatography (100 g basic silica using a 5% to 50% EtOAc in heptanes gradient)

Sources & evidence

ORD record
ord-b67d683d662a480787ac0d63093fc81b
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

Loading…