Reaktion #1533997

Reaktionsgleichung

n-butyllithium

1,4-dioxaspiro(4.5)decan-8-one

2-bromodiphenylmethane

→

8-[2-(phenylmethyl)phenyl]-1,4-dioxaspiro(4.5)decan-8-ol

Ausbeute 42.3%

Lösungsmittel

n-hexane

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONafter addition
2. 2
   workup.STIRRINGThis mixture is stirred overnight (16 hours) at -70° C. to +10° C.
3. 3
   Sonstigequenched with 50 ml of water
4. 4
   workup.ADDITIONThe organic phase is diluted with 100 ml of ether
5. 5
   Waschenwashed three times with 50 ml portions of water
6. 6
   ExtraktionThe aqueous phase and the washing water are extracted with 100 ml of CH2Cl2, which
7. 7
   Waschenis washed twice with 50 ml portions of water
8. 8
   TrocknenThe combined organic phases are dried over Na2SO4
9. 9
   Sonstigeevaporated to an oil
10. 10
    workup.ADDITIONThis oil is treated with ether/hexane (20 ml/50 ml) mixture
11. 11
    Sonstigeto give 6.0 g (45.8%) yield of crystalline product which
12. 12
    Sonstigeis recrystallized from ether/hexane (10 ml/40 ml)

Vorschrift

26.25 ml of 2.4 molar solution of n-butyllithium in n-hexane is added dropwise with stirring at -50° to -40° C. under dry nitrogen to a solution of 10.87 g of 2-bromodiphenylmethane in 25 ml of dry THF. The mixture is stirred at -50° to -40° C. for one hour after addition is completed. A solution of 6.30 g of 1,4-dioxaspiro(4.5)decan-8-one in 20 ml of dry THF is added dropwise at -50° to -40° C. This mixture is stirred overnight (16 hours) at -70° C. to +10° C., and quenched with 50 ml of water. The organic phase is diluted with 100 ml of ether and washed three times with 50 ml portions of water. The aqueous phase and the washing water are extracted with 100 ml of CH2Cl2, which is washed twice with 50 ml portions of water. The combined organic phases are dried over Na2SO4 and evaporated to an oil. This oil is treated with ether/hexane (20 ml/50 ml) mixture to give 6.0 g (45.8%) yield of crystalline product which is recrystallized from ether/hexane (10 ml/40 ml) to provide 5.53 g (42.2% yield) of 8-[2-(phenylmethyl)phenyl]-1,4-dioxaspiro(4.5)decan-8-ol, m.p. 97°-98° C.

Quelle