Reaktion #6086

Reaktionsgleichung

2-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]pyridine-5-carboxaldehyde

ethylmagnesium bromide

→

title compound

2-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]-5-(1-hydroxypropyl)pyridine

Lösungsmittel

ether

ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefitted with a mechanical stirrer, a reflux condenser
2. 2
   Sonstigeprotected by a drying tube
3. 3
   Sonstigeprotected by a drying tube
4. 4
   TemperaturThe flask is cooled in an ice-bath
5. 5
   SonstigeThe cooling bath is then removed
6. 6
   Temperaturthe mixture heated
7. 7
   Temperaturat reflux for 3 hours
8. 8
   TemperaturThe mixture is then cooled in an ice-salt bath
9. 9
   workup.ADDITION5 ml of saturated ammonium chloride solution is added
10. 10
    Filtrationfiltered
11. 11
    Waschenthe residue washed with two 10 ml portions of ether
12. 12
    SonstigeThe ether solution is then separated
13. 13
    Trocknendried (MgSO4)
14. 14
    Sonstigethe ether removed in vacuo
15. 15
    SonstigeThe residue is then purified by chromatography
16. 16
    Sonstigefollowed by recrystallization

Vorschrift

Four ml of a 3M (12 mmol) solution of ethylmagnesium bromide in ether is placed in a 3-necked flask fitted with a mechanical stirrer, a reflux condenser protected by a drying tube and a pressure-equalizing dropping funnel protected by a drying tube. The flask is cooled in an ice-bath and a solution of 3.174 g (10 mmol) of 2-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]pyridine-5-carboxaldehyde in 10 ml of dry ether is added slowly with vigorous stirring. The cooling bath is then removed and the mixture heated at reflux for 3 hours. The mixture is then cooled in an ice-salt bath and 5 ml of saturated ammonium chloride solution is added. The mixture is stirred for a further 1 hour and then filtered and the residue washed with two 10 ml portions of ether. The ether solution is then separated, dried (MgSO4) and the ether removed in vacuo. The residue is then purified by chromatography followed by recrystallization to give the title compound.

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