Reaktion #54572

Reaktionsgleichung

ether

methyl lithium

3,4-dihydro-7-hydroxy-4-(1-naphthyl)coumarin

ether

→

4-(2,4-dihydroxyphenyl)-2-methyl-4-(1-naphthyl)-2-butanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONthe solid material gradually dissolved
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Temperaturunder reflux for 4 hours
4. 4
   Temperaturthen cooled
5. 5
   workup.ADDITIONpoured into acid
6. 6
   ExtraktionThe ether extract

Vorschrift

To a stirred solution of methyl lithium in ether (80 ml, 1.9 M solution) at ambient temperature under nitrogen was added portionwise over 0.5 hour finely divided 3,4-dihydro-7-hydroxy-4-(1-naphthyl)coumarin (7.52 g). The ether boiled during the addition and the solid material gradually dissolved. After the addition was complete the solution was boiled under reflux for 4 hours then cooled and poured into acid. The ether extract yielded 4-(2,4-dihydroxyphenyl)-2-methyl-4-(1-naphthyl)-2-butanol which was dissolved in glacial acetic acid (55 ml) and boiled under reflux overnight. The product was poured into water (200 ml) and extracted into ether. The ether extract was washed with water and aqueous sodium bicarbonate then dried (magnesium sulphate). Removal of the solvent gave the title compound (7.70 g) as a foam containing some ether.

Quelle