EThyl (2E)-3-(2,6-dichloropyridin-3-yl)prop-2-enoate → Ethyl 3-(2,6-dichloropyridin-3-yl)propanoate

HRID 595738Notes

Reaction equation

HRID 595738 reaction equation
[Cl:1][C:2]1[C:7](/[CH:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=[C:4]([Cl:15])[N:3]=1>C(O)C.[Pt]>[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=[C:4]([Cl:15])[N:3]=1

Participants

4

Reactant 1

HCID 90341030EThyl (2E)-3-(2,6-dichloropyridin-3-yl)prop-2-enoate

Product 1

HCID 23157101Ethyl 3-(2,6-dichloropyridin-3-yl)propanoate

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (E)-ethyl 3-(2,6-dichloropyridin-3-yl)acrylate (500 mg, 2.032 mmol) in Ethanol (15 mL) was added 10% platinum on carbon (96 mg, 0.049 mmol). The flask was alternately evacuated and filled with hydrogen five times. The solution was stirred under 1 ATM (balloon) of hydrogen for 1 h, then filtered through celite, while washing well with MeOH and EtOAc. The filtrate was concentrated in vacuo to provide the title compound which was used without further purification. 1H NMR δ (ppm) (CHCl3-d): 7.62 (1H, d, J=7.92 Hz), 7.24 (1H, d, J=7.8), 4.15 (2H, q, J=7.15 Hz), 3.05 (2H, t, J=7.35 Hz), 2.69 (2H, t, J=7.35 Hz), 1.31˜1.24 (3H, m). MS (M+H)+: 247.

Workup

  1. customThe flask was alternately evacuated
  2. additionfilled with hydrogen five times
  3. filtrationfiltered through celite
  4. washwhile washing well with MeOH and EtOAc
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-71a46f509ddc43f49f4d5b1ca5df13bb
Source dataset
uspto-grants-2016_01
Patent number
US09243002B2

Reaction notes

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