6-Methoxypyridine-3-carbaldehyde → Ethyl 3-(6-methoxy-3-pyridyl)acrylate

HRID 1905911Notes

Reaction equation

HRID 1905911 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=O)=[CH:5][CH:4]=1.[C:11]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:12]C([O-])=O>N1CCCCC1.N1C=CC=CC=1>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]=[CH:12][C:11]([O:17][CH2:18][CH3:19])=[O:16])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 33645766-Methoxypyridine-3-carbaldehydeHCID 3595298Propanedioic acid, monoethyl ester

Product 1

HCID 53930754Ethyl 3-(6-methoxy-3-pyridyl)acrylateYield 79.2%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 6-methoxypyridine-3-carboxaldehyde (2.34 g), monoethyl malonate (4.51 g), pyridine (12 ml) and piperidine (6 drops) was heated under reflux for 5 hours and was evaporated to an oil. This oil was partitioned between ether and dilute aqueous ammonia. The ether layer was washed with water and evaporated to an oil which crystallised on standing to give ethyl 3-(6-methoxy-3-pyridyl)acrylate (2.8 g, 79%) m.p. 49°-52°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customwas evaporated to an oil
  4. customThis oil was partitioned between ether and dilute aqueous ammonia
  5. washThe ether layer was washed with water
  6. customevaporated to an oil which
  7. customcrystallised

Sources & evidence

ORD record
ord-364a3ff8ffc24e1b8e04770ec801929c
Source dataset
uspto-grants-1987_03
Patent number
US04649141

Reaction notes

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