Triethylamine → 5-Ethenyl-2-methoxypyridine

HRID 859731Notes

Reaction equation

HRID 859731 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-c111959df1e046f39201f27278aab74a
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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