2-Vinylpyridine → HCID 66837013, compound

HRID 1777793Notes

Reaction equation

HRID 1777793 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[CH2:2].[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-]>C1(C)C=CC=CC=1>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C@@H:1]1[CH2:2][C@H:11]1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 75212-VinylpyridineHCID 12192Ethyl diazoacetate

Product 1

HCID 66837013HCID 66837013, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-vinylpyridine (13-1) (2 g, 19.0 mmol) in toluene (40 ml) was treated with ethyl diazoacetate (1.97 ml, 19.0 mmol) and stirred at reflux overnight. The mixture was concentrated in vacuo, and the residue was purified by gradient elution on silica gel (0-50% EtOAc/hexanes) to elute peak 1; the solvent gradient was then ramped to 100% EtOAc to elute peak 2. This yielded the 13-3 (1.6 g, 44%) as the first eluting diastereomer, and the corresponding cis diastereomer 13-2 (914 mg, 25%) as the second eluting diastereomer, both as yellow oils. 1H NMR (500 MHz, CDCl3): δ 8.44 (m, 1H), 7.56 (dt, J=7.6, 1.7 Hz, 1H), 7.22 (dd, J=7.8, 1.0 Hz, 1H), 7.08 (ddd, J=7.6, 4.9, 1.2 Hz, 1H), 4.17 (q, J=7.3 Hz, 2H), 2.58 (ddd, J=10.0, 6.1, 3.9 Hz, 1H), 2.25 (ddd, J=9.5, 5.6, 3.9 Hz, 1H), 1.61, (m, 2H), 1.28 (t, J=7.1 Hz, 3H). LC/MS: m/z (M+H)=192.1.

Workup

  1. temperatureat reflux overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by gradient elution on silica gel (0-50% EtOAc/hexanes)
  4. washto elute peak 1
  5. washto elute peak 2

Sources & evidence

ORD record
ord-0a2d919cbd104aedb88f5c65ef69b5a4
Source dataset
uspto-grants-2016_02
Patent number
US09266881B2

Reaction notes

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