Water → 3-[(Cyclopent-3-en-1-yl)methyl]-2-methoxypyridine

HRID 1727187Notes

Reaction equation

HRID 1727187 reaction equation
[CH:1]1([C:6]([C:8]2[C:9]([O:14][CH3:15])=[N:10][CH:11]=[CH:12][CH:13]=2)=O)[CH2:5][CH:4]=[CH:3][CH2:2]1.[OH-].[K+].NN.O>C(O)CO>[CH:1]1([CH2:6][C:8]2[C:9]([O:14][CH3:15])=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:2][CH:3]=[CH:4][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 59837860(Cyclopent-3-en-1-yl)(2-methoxypyridin-3-yl)methanone

Product 1

HCID 598378653-[(Cyclopent-3-en-1-yl)methyl]-2-methoxypyridineYield 51%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Cyclopent-3-en-yl[2-(methyloxy)pyridin-3-yl]methanone (Preparation 29, 10 g, 49.3 mmol), potassium hydroxide (85%, 16.8 g, 0.3 mol), and hydrazine (6.33 g, 198 mmol) in ethylene glycol (100 ml) were heated to 180° C. and stirred for 18 h. Water was added and the product was extracted with hexane:ethyl acetate (50:50). The combined organic extracts were washed with brine and concentrated in vacuo. The crude oil was purified by flash chromatography eluting with ethyl acetate:hexane (10:90) to give a colourless oil (4.75 g, 51%).

Workup

  1. extractionthe product was extracted with hexane:ethyl acetate (50:50)
  2. washThe combined organic extracts were washed with brine
  3. concentrationconcentrated in vacuo
  4. customThe crude oil was purified by flash chromatography
  5. washeluting with ethyl acetate:hexane (10:90)

Sources & evidence

ORD record
ord-9a5e9d43e77a408683a8e74c60737be8
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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