Triethylamine → 5-Ethenyl-2-methoxypyridine

HRID 2387121Notes

Reaction equation

HRID 2387121 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9](O)[CH3:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.CS(Cl)(=O)=O>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]=[CH2:10])=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 450909001-(6-Methoxypyridin-3-yl)ethanol

Product 1

HCID 230701355-Ethenyl-2-methoxypyridineYield 37.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(6-methoxy-pyridin-3-yl)-ethanol (14.3 g, 93.5 mmol) in anhydrous THF was added triethylamine (32.3 mL), followed by MsCl (8.6 mL, 112 mmol). The resulting mixture was stirred at room temperature for 15 hours before it was filtered through a pad of celite. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography to afford the desired product (4.7 g, 37% yield). 1H NMR (300 MHz, CDCl3): δ 3.94 (s, 3 H), 5.20-5.23 (m, 1H), 5.61-5.67 (m, 1 H), 6.60-6.78 (m, 2 H), 7.67-7.72 (m, 1 H), 8.12 (s, 1 H).

Workup

  1. filtrationwas filtered through a pad of celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-58c77e2b5d60400398e4fdd818c0f102
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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